Triethylamine → HCID 86691633, compound

HRID 624323Notes

Reaction equation

HRID 624323 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([C:25]4[CH:26]=[CH:27][C:28]([O:34][CH3:35])=[C:29]([CH:33]=4)[C:30]([OH:32])=O)=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)=[CH:4][CH:3]=1.Cl.[N:37]1[CH:42]=[CH:41][CH:40]=[N:39][C:38]=1[C:43]1([NH2:46])[CH2:45][CH2:44]1.C(N(CC)CC)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([C:25]4[CH:26]=[CH:27][C:28]([O:34][CH3:35])=[C:29]([CH:33]=4)[C:30]([NH:46][C:43]4([C:38]5[N:39]=[CH:40][CH:41]=[CH:42][N:37]=5)[CH2:45][CH2:44]4)=[O:32])=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 569656581-(Pyrimidin-2-yl)cyclopropan-1-amine hydrochlorideHCID 86691632HCID 86691632, compound

Product 1

HCID 86691633HCID 86691633, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 5-(2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoic acid (300 mg, 0.634 mmol) and 1-(pyrimidin-2-yl)cyclopropanamine hydrochloride (131 mg, 0.760 mmol) in DMF (15 mL) at room temperature under a nitrogen atmosphere was added triethylamine (TEA) (0.442 mL, 3.17 mmol). The mixture was cooled to 0° C. and added with BOP reagent (420 mg, 0.951 mmol). The reaction mixture was then stirred at rt overnight, and then diluted with water. The solid was filtered and dried under suction to obtain the title compound as a light yellow solid. Yield: 350 mg (94%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.52 (br. s, 1H) 8.93 (s, 1H) 8.70 (s, 2 H) 8.49 (s, 1H) 8.00-8.14 (m, 2H) 7.88 (d, J=2.51 Hz, 1H) 7.74 (s, 1H) 7.52 (dd, J=8.53, 2.51 Hz, 1H) 7.34-7.43 (m, 4H) 7.20 (s, 1H) 3.89 (s, 3H) 1.54-1.68 (m, 2H) 1.36-1.49 (m, 2H). LCMS: (ES+) m/z=591.39 (M+H)+; Column—ACQUITY UPLC BEH C8 (50×2.1 mm; 1.7 μm); Mphase A: 5 mM Ammonium Acetate:MeCN (95:5); Mphase B: 5 mM Ammonium Acetate: MeCN (5:95)

Workup

  1. filtrationThe solid was filtered
  2. customdried under suction

Sources & evidence

ORD record
ord-8d85b902effa44099271ec585aa35e3d
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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