4-Methylmorpholine → Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylcarbamate

HRID 2361338Notes

Reaction equation

HRID 2361338 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([F:39])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:36](O)=[O:37])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].F[P-](F)(F)(F)(F)F.[N:49]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.CN1CCOCC1>CN(C=O)C.O>[C:36]([C:21]1[C:22]2[NH:23][C:24]3[C:29]([C:30]=2[C:18]([C:14]2[C:13]([F:39])=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:17]=[CH:16][CH:15]=2)=[CH:19][N:20]=1)=[CH:28][CH:27]=[C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])[CH:25]=3)(=[O:37])[NH2:49]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 679948974-(3-(Benzyloxycarbonylamino)-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid

Product 1

HCID 67994974Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylcarbamateYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A burgundy, homogeneous solution of 4-(3-(benzyloxycarbonylamino)-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.7 g, 1.322 mmol), ammonium chloride (0.283 g, 5.29 mmol), BOP (0.760 g, 1.719 mmol), DIPEA (1.108 mL, 6.35 mmol) and N-methylmorpholine (0.567 mL, 5.16 mmol) in DMF (8 mL) under nitrogen was stirred. After 2 hr, water (20 mL) was added, and the reaction was stirred at room temperature for 45 min. The precipitate was collected, rinsed with water and dried over Drierite under vacuum to give the desired product (0.6318 g, 1.195 mmol, 90% yield) as a tan solid.

Workup

  1. customThe precipitate was collected
  2. washrinsed with water
  3. dry with materialdried over Drierite under vacuum

Sources & evidence

ORD record
ord-f87961b347f54b8aaf94a6a7ddb230d8
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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