1,4-Dioxaspiro[4.5]decan-8-one → N-(1-(4-oxocyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

HRID 2175589Notes

Reaction equation

HRID 2175589 reaction equation
O1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)OCC1.[NH:12]1[CH2:15][CH:14]([NH:16][C:17](=[O:34])[CH2:18][NH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[O:11]=[C:8]1[CH2:7][CH2:6][CH:5]([N:12]2[CH2:13][CH:14]([NH:16][C:17](=[O:34])[CH2:18][NH:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([F:31])([F:33])[F:32])[CH:28]=4)[N:23]=[CH:22][N:21]=3)[CH2:15]2)[CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydrideHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 54770393N-(1-(4-oxocyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Procedure

Reaction of 1,4-dioxaspiro[4.5]decan-8-one 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 followed by acidic deprotection of the ketal afforded the product.

Workup

  1. customafforded the product

Sources & evidence

ORD record
ord-0b5330eda2034a89bb4e06780e37dd09
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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