Triethylamine → HCID 53260082, compound

HRID 1992118Notes

Reaction equation

HRID 1992118 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:16][CH2:17][N:18]3[CH:23]4[CH2:24][CH2:25][CH:19]3[CH2:20][CH:21]([N:26]3[C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=5[N:28]=[C:27]3[CH3:35])[CH2:22]4)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[F:36].C(N(CC)CC)C.[Cl:44][C:45]1[CH:53]=[CH:52][C:48]([C:49]([OH:51])=[O:50])=[CH:47][C:46]=1[S:54](=[O:57])(=[O:56])[NH2:55].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[OH-:50].[NH4+:13].[Cl:44][C:45]1[CH:53]=[CH:52][C:48]([C:49]([N:13]2[CH2:12][CH2:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([Cl:3])=[C:5]([F:36])[CH:6]=3)([CH2:16][CH2:17][N:18]3[C@H:19]4[CH2:25][CH2:24][C@@H:23]3[CH2:22][CH:21]([N:26]3[C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=5[N:28]=[C:27]3[CH3:35])[CH2:20]4)[CH2:15][CH2:14]2)=[O:51])=[CH:47][C:46]=1[S:54]([NH2:55])(=[O:57])=[O:56]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 145684-Chloro-3-sulfamoylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68676149HCID 68676149, compound

Product 2

HCID 14923Ammonium HydroxideHCID 53260082HCID 53260082, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(8-{2-[4-(4-chloro-3-fluoro phenyl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole dihydrochloride (0.40 g, 0.78 mmol), triethylamine (0.35 mL, 2.5 mmol) and 4-chloro-3-sulfamoylbenzoic acid (184 mg, 0.78 mmol) in dimethylformamide (2.5 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (327 mg, 0.86 mmol) and the resulting mixture was stirred for 1 h at rt. The mixture was diluted with water and the resulting precipitate was collected, washed with saturated sodium bicarbonate solution, with water, dried and purified by chromatography on silica gel eluting with a 400:15:1 to 200:15:1 gradient of chloroform:methanol:ammonium hydroxide to give 2-chloro-5-[(4-(4-chloro-3-fluoro phenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}piperidin-1-yl)carbonyl]benzenesulfonamide as a solid (0.24 g, 43%). 1H NMR (400 MHz, CD3OD) δ 8.09 (s, 1H), 7.68 (m, 1H), 7.61 (m, 1H), 7.34-7.54 (m, 4H), 7.17-7.26 (m, 3H), 4.73 (m, 1H), 4.09 (m, 1H), 3.59 (m, 1H), 3.43 (m, 1H), 3.30 (m, 3H), 2.53 (s, 3H), 2.40-2.48 (m, 4H), 2.28 (m, 1H), 2.16 (m, 1H), 1.83-2.04 (m, 10H), 1.70 (m, 2H). HRMS C35H38Cl2FN5O3S m/z 698.2135 (M+H)Cal., 698.2142 (M+H)Obs..

Workup

  1. customthe resulting precipitate was collected
  2. washwashed with saturated sodium bicarbonate solution, with water
  3. customdried
  4. custompurified by chromatography on silica gel eluting with a 400:15:1 to 200:15:1 gradient of chloroform

Sources & evidence

ORD record
ord-6985a5fdde8b456c9469b060a884e103
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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