Sodium triacetoxyborohydride → HCID 86660466, compound

HRID 2175596Notes

Reaction equation

HRID 2175596 reaction equation
C([CH:3]1[CH2:8][CH:7]([C:9]([F:12])([F:11])[F:10])[CH2:6][CH2:5][C:4]1=O)C.[NH:14]1[CH2:17][CH:16]([NH:18][C:19](=[O:36])[CH2:20][NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:32]([F:35])([F:34])[F:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)[CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[F:10][C:9]([F:12])([F:11])[CH:7]1[CH2:8][CH2:3][CH:4]([N:14]2[CH2:15][CH:16]([NH:18][C:19](=[O:36])[CH2:20][NH:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([C:32]([F:34])([F:33])[F:35])[CH:30]=4)[N:25]=[CH:24][N:23]=3)[CH2:17]2)[CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamideHCID 68003866HCID 68003866, compound

Product 1

HCID 86660466HCID 86660466, compound

Procedure

Reaction of ethyl 4-(trifluoromethyl)cyclohexanone 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 (CHLOROFORM-d) δ: 8.60 (s, 1 H), 8.21 (t, J=5.4 Hz, 1 H), 8.12 (s, 1 H), 7.71-7.81 (m, 2 H), 6.92 (d, J=7.8 Hz, 1 H), 4.49-4.66 (m, 1 H), 4.28 (d, J=5.6 Hz, 2 H), 3.57 (t, J=7.5 Hz, 2 H), 2.85-3.00 (m, 2 H), 2.31 (t, J=3.2 Hz, 1 H), 1.89-2.14 (m, 2 H), 1.53-1.78 (m, 5 H), 1.28-1.42 (m, 2 H); ESI-MS (m/z): Calcd. For C21H23F6N5O: 475.18. found: 476 (M+H).

Workup

  1. customafforded the product

Sources & evidence

ORD record
ord-321dbf88db47472e84f9a190e3b7552f
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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