Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178481210, compound

HRID 1410257Notes

Reaction equation

HRID 1410257 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:39])=[CH:5][C:6]([Cl:38])=[C:7]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[C:17]([O:33][CH2:34][CH:35]([F:37])[F:36])[C:18]([C:20]([NH:22][C@H:23]4[CH2:28][CH2:27][C@H:26]([C:29]([F:32])([F:31])[F:30])[CH2:25][CH2:24]4)=[O:21])=[CH:19][C:12]=3[N:11]=2)[CH:8]=1.[F:40][C:41]([F:49])([F:48])[C:42]1([C:45](O)=[O:46])[CH2:44][CH2:43]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:38][C:6]1[CH:5]=[C:4]([F:39])[C:3]([CH2:2][NH:1][C:45]([C:42]2([C:41]([F:49])([F:48])[F:40])[CH2:44][CH2:43]2)=[O:46])=[CH:8][C:7]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[CH:16]=[C:17]([O:33][CH2:34][CH:35]([F:36])[F:37])[C:18]([C:20]([NH:22][C@H:23]3[CH2:28][CH2:27][C@H:26]([C:29]([F:31])([F:32])[F:30])[CH2:25][CH2:24]3)=[O:21])=[CH:19][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 178481208HCID 178481208, compound

Product 1

HCID 178481210HCID 178481210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in accordance with the procedure in Example 72, step (c) using 2-[5-(aminomethyl)-2-chloro-4-fluoro-phenyl]amino-6-(2,2-difluoroethoxy)-1-methyl-N-(trans-4-trifluoromethyl-cyclohex-1-yl)-1H-benzo[d]imidazole-5-carboxamide (150 mg; 0.26 mmol), 1-(trifluoromethyl)-cyclopropanecarboxylic acid (40 mg; 0.26 mmol), HBTU (99 mg; 0.26 mmol), TEA (53 mg; 0.52 mmol) and DMF (4 mL). Yield: 39 mg (21%). 400 MHz 1H-NMR (DMSO-d6, ppm) 8.40 (1H, t, J=5.8 Hz) 8.32 (1H, s) 7.90-7.82 (2H, m) 7.78-7.74 (1H, m) 7.44 (1H, d, J=9.6 Hz) 7.23-7.19 (1H, m) 6.63-6.34 (1H, m) 4.51-4.40 (2H, m) 4.29 (2H, d, J=5.8 Hz) 3.78-3.65 (4H, m) 2.28-2.17 (1H, m) 2.03-1.97 (2H, m) 1.91-1.85 (2H, m) 1.39-1.19 (8H, m). MS m/z: 714, 716 [M+H]+.

Sources & evidence

ORD record
ord-e6ca777ac85f4f20976f7c96a8f61c73
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

Loading…