Sodium triacetoxyborohydride → HCID 54769306, compound

HRID 2175597Notes

Reaction equation

HRID 2175597 reaction equation
[CH2:1]([NH:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[NH:13]1[CH2:16][CH:15]([NH:17][C:18](=[O:35])[CH2:19][NH:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH2:1]([NH:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([N:13]2[CH2:14][CH:15]([NH:17][C:18](=[O:35])[CH2:19][NH:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:32])([F:34])[F:33])[CH:29]=4)[N:24]=[CH:23][N:22]=3)[CH2:16]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamideHCID 68003599HCID 68003599, compound

Product 1

HCID 54769306HCID 54769306, compound

Procedure

Reaction of N-ethyl-4-oxocyclohexanecarboxamide with N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide (as prepared in Example 1 Step G) in the presence of TEA and NaBH(OAc)3 as described in Example 1, Step H afforded the product. 1H NMR (DMSO-d6) δ: 0.97 (t, J=7.20 Hz, 3 H) 1.25 (d, J=16.93 Hz, 5 H) 1.48 (br. s., 2 H) 1.67 (br. s., 2 H) 1.97-2.08 (m, 1 H) 2.17 (br. s., 1 H) 2.74 (t, J=7.07 Hz, 2 H) 3.01 (m, J=7.07, 5.81 Hz, 2 H) 3.43 (t, J=7.20 Hz, 2 H) 4.12 (d, J=5.56 Hz, 2 H) 4.17-4.30 (m, 1 H) 7.61 (t, J=5.56 Hz, 1 H) 7.88 (d, J=8.59 Hz, 1 H) 8.05 (dd, J=8.97, 1.39 Hz, 1 H) 8.44 (d, J=7.33 Hz, 1 H) 8.55 (s, 1 H) 8.81 (s, 1 H) 9.05 (t, J=5.43 Hz, 1 H); ESI-MS (m/z): Calcd. For C23H29F3N6O2: 478.23. found: 479 (M+H).

Workup

  1. customafforded the product

Sources & evidence

ORD record
ord-cb7fb894823d4dbbae2f62ca34a6acce
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

Loading…