HCID 58691359, compound → HCID 58691309, compound

HRID 1594481Notes

Reaction equation

HRID 1594481 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[N:20]=[CH:19][N:18]=[C:17]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=4[NH:31][C:32]([C@H:34]4[CH2:39][CH2:38][CH2:37][CH2:36][N:35]4[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:33])[CH:16]=3)[C:8]=2[N:9]=1)(=[O:3])[CH3:2].C(NC1SC2C=CC=C(OC3N=CN=C(C4C=CC(C(F)(F)F)=CC=4NC([C@@H]4CCCCN4CC(C)C)=O)C=3)C=2N=1)(=O)C>>[C:1]([NH:4][C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[N:20]=[CH:19][N:18]=[C:17]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][C:22]=4[NH:31][C:32]([CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][N:35]4[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:33])[CH:16]=3)[C:8]=2[N:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 58691359HCID 58691359, compoundHCID 58691392HCID 58691392, compound

Product 1

HCID 58691309HCID 58691309, compound

Procedure

(2R)-N-(2-(6-(2-Acetamidobenzo[d]thiazol-4-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenyl)-1-isobutylpiperidine-2-carboxamide and (2S)-N-(2-(6-(2-Acetamidobenzo[d]thiazol-4-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenyl)-1-isobutylpiperidine-2-carboxamide. Chiral separation [Chiralcel OD-H (250×21 mm, 5μ), A: hexane (0.2% diethylamine), B: ethanol (0.2% diethylamine), isocratic: 60:40 A:B, 20 mL/min] of N-(2-(6-(2-acetamidobenzo[d]-thiazole-4-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenyl)-1-isobutylpiperidine-2-carboxamide (Example 51) afforded the title compounds as amorphous solids. MS (ESI, pos. ion) m/z: 613 (M+1).

Workup

  1. customChiral separation [Chiralcel OD-H (250×21 mm, 5μ)

Sources & evidence

ORD record
ord-87ea432abaa24f599970c9c2e1a11888
Source dataset
uspto-grants-2007_11
Patent number
US07301022B2

Reaction notes

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