1,4-Dioxaspiro[4.5]decan-8-one → N-(1-(4-hydroxy-4-(2-methylthiazol-5-yl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

HRID 1896904Notes

Reaction equation

HRID 1896904 reaction equation
[OH:1][C:2]1([C:9]2[S:13][C:12]([CH3:14])=[N:11][CH:10]=2)[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.BrC1SC(C)=NC=1.O1C2(CCC(=O)CC2)OCC1.[NH:33]1[CH2:36][CH:35]([NH:37][C:38](=[O:55])[CH2:39][NH:40][C:41]2[C:50]3[C:45](=[CH:46][CH:47]=[C:48]([C:51]([F:54])([F:53])[F:52])[CH:49]=3)[N:44]=[CH:43][N:42]=2)[CH2:34]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[OH:1][C:2]1([C:9]2[S:13][C:12]([CH3:14])=[N:11][CH:10]=2)[CH2:7][CH2:6][CH:5]([N:33]2[CH2:34][CH:35]([NH:37][C:38](=[O:55])[CH2:39][NH:40][C:41]3[C:50]4[C:45](=[CH:46][CH:47]=[C:48]([C:51]([F:52])([F:54])[F:53])[CH:49]=4)[N:44]=[CH:43][N:42]=3)[CH2:36]2)[CH2:4][CH2:3]1

Participants

6

Reactant 5

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydrideHCID 132286635-Bromo-2-methyl-1,3-thiazoleHCID 59017431HCID 59017431, compoundHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 68004012N-(1-(4-hydroxy-4-(2-methylthiazol-5-yl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Procedure

Reaction of 4-hydroxy-4-(2-methylthiazol-5-yl)cyclohexanone (prepared by the reaction of 5-bromo-2-methylthiazole with 1,4-dioxaspiro[4.5]decan-8-one using the sequence described in Example 24 Step A-B) 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-461d9a1399894b9ebfa78414928b1a5d
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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