Sodium triacetoxyborohydride → Ethyl 2-(4-(3-(2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamido)azetidin-1-yl)cyclohexyl)acetate

HRID 1896917Notes

Reaction equation

HRID 1896917 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.[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:35][C:32]([F:33])([F:34])[C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][N:23]=[C:22]2[NH:21][CH2:20][C:19]([NH:18][CH:16]1[CH2:17][N:14]([CH:2]2[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]2)[CH2:15]1)=[O:36]

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12666966Ethyl 2-(4-oxocyclohexyl)acetateHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 68004047Ethyl 2-(4-(3-(2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamido)azetidin-1-yl)cyclohexyl)acetate

Procedure

Reaction of ethyl 2-(4-oxocyclohexyl)acetate 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.

Workup

  1. customafforded the product

Sources & evidence

ORD record
ord-f67192a785b0409aa9bcd88deec48a80
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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