Lithium Hydroxide → HCID 178445690, compound

HRID 1717704Notes

Reaction equation

HRID 1717704 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12](OC)=[O:13])[O:8][CH2:7][CH2:6][CH:5]2[N:16]([C@H:31]1[CH2:36][CH2:35][C@H:34]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:33][CH2:32]1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=1)=[O:18].[Li+].[OH-].[NH2:43][C:44]1[NH:48][N:47]=[N:46][N:45]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([NH:43][C:44]1[NH:48][N:47]=[N:46][N:45]=1)=[O:13])[O:8][CH2:7][CH2:6][CH:5]2[N:16]([C@H:31]1[CH2:36][CH2:35][C@H:34]([C:37]([CH3:39])([CH3:40])[CH3:38])[CH2:33][CH2:32]1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:29])([F:28])[F:30])=[CH:22][CH:21]=1)=[O:18]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 178496889HCID 178496889, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178445690HCID 178445690, compound

Procedure

Enantiomer A of methyl 6-bromo-4-[(trans-4-tert-butylcyclohexyl)({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]chromane-7-carboxylate (25 mg) was saponified with aqueous LiOH and then coupled to 5-amino tetrazole following the procedure described (Step D., Example 1/2) to give 6-bromo-4-[(trans-4-tert-butylcyclohexyl)({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-N-1H-tetrazol-5-ylchromane-7-carboxamide. HPLC/MS: m/z=680.2 (M+1), Rt=2.55 min. 1H NMR (DMSO-d6): δ 12.58 (1H, br s), 8.61 (1H, s), 7.47 (2H, dd, J=2.5 Hz, 8.5 Hz), 7.29 (1H, s), 7.21 (2H, d, J=8.5 Hz), 7.05 (1H, s), 4.71 (1H, m), 4.40 (1H, dt, J=2.5 Hz, 10.5 Hz), 4.25 (1H, t, J=10.5 Hz), 3.93 (1H, m), 2.77 (1H, m), 2.02 (1H, m), 1.90-1.67 (6H, m), 1.29-1.03 (4H, m), 0.88 (9H, s).

Sources & evidence

ORD record
ord-9f4160de904f45c9ac76203e36dbfccf
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

Loading…