Methanol → (9-(3-(2-Hydroxyethyl)benzyl)-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

HRID 471285Notes

Reaction equation

HRID 471285 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:7][NH:6][CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][OH:22])[CH:17]=[CH:18][CH:19]=3)[CH2:9][CH2:8]2)[O:3]1.[CH3:24][C:25]1[S:26][CH:27]=[C:28]([C:30](O)=[O:31])[N:29]=1.CO.C(N(CC)CC)C>ClCCl>[OH:22][CH2:21][CH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][N:10]1[CH2:11][CH2:12][C:4]2([O:3][C:2]([CH3:23])([CH3:1])[CH2:7][N:6]([C:30]([C:28]3[N:29]=[C:25]([CH3:24])[S:26][CH:27]=3)=[O:31])[CH2:5]2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 2847282-Methyl-1,3-thiazole-4-carboxylic acidHCID 579890912-(3-((2,2-Dimethyl-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)ethanol

Product 1

HCID 57989096(9-(3-(2-Hydroxyethyl)benzyl)-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The subtitled compound was prepared using a similar method to that described in Example 22 step (a) using 2-(3-((2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)ethanol (0.2 g) (Example 271, step e) and 2-methylthiazole-4-carboxylic acid (0.09 g). The reaction mixture was stirred for 18 h, and the elution solvent for the chromatography was 2% methanol in dichloromethane with 1% triethylamine. Yield 0.16 g

Sources & evidence

ORD record
ord-aa522202867040d8ae75e52950a116dc
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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