1,4-Dioxaspiro[4.5]decan-8-one → HCID 68004010, compound

HRID 1896905Notes

Reaction equation

HRID 1896905 reaction equation
[OH:1][C:2]1([C:9]2[S:13][C:12]([CH:14]([CH3:16])[CH3:15])=[N:11][CH:10]=2)[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.BrC1SC(C(C)C)=NC=1.O1C2(CCC(=O)CC2)OCC1.[NH:37]1[CH2:40][CH:39]([NH:41][C:42](=[O:59])[CH2:43][NH:44][C:45]2[C:54]3[C:49](=[CH:50][CH:51]=[C:52]([C:55]([F:58])([F:57])[F:56])[CH:53]=3)[N:48]=[CH:47][N:46]=2)[CH2:38]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[OH:1][C:2]1([C:9]2[S:13][C:12]([CH:14]([CH3:16])[CH3:15])=[N:11][CH:10]=2)[CH2:7][CH2:6][CH:5]([N:37]2[CH2:38][CH:39]([NH:41][C:42](=[O:59])[CH2:43][NH:44][C:45]3[C:54]4[C:49](=[CH:50][CH:51]=[C:52]([C:55]([F:56])([F:58])[F:57])[CH:53]=4)[N:48]=[CH:47][N:46]=3)[CH2:40]2)[CH2:4][CH2:3]1

Participants

6

Reactant 5

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydrideHCID 20696775HCID 20696775, compoundHCID 595561884-Hydroxy-4-(2-isopropylthiazol-5-yl)cyclohexanoneHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 68004010HCID 68004010, compound

Procedure

Reaction of 4-hydroxy-4-(2-isopropylthiazol-5-yl)cyclohexanone (prepared by the reaction of 5-bromo-2-isopropylthiazole 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-aa6a6b66f48448ed9a4a7ed8c29d7c75
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

Loading…