Tert-butyl 4-hydroxypiperidine-1-carboxylate → N-(5-(azepan-4-yloxy)isothiazol-4-yl)-2-(2,6-difluorophenyl)thiazole-4-carboxamide

HRID 871040Notes

Reaction equation

HRID 871040 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](OC(C)(C)C)=O)[CH2:4][CH2:3]1.OC1CCC[N:19](C(OC(C)(C)C)=O)CC1.N[C:31]1[S:35][C:34]([C:36]2[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:37]=2[F:43])=[N:33][C:32]=1[C:44]([OH:46])=O.FC1C=CC=C(F)C=1C1[S:56][CH:57]=[C:58]([C:60](O)=O)[N:59]=1>>[NH:5]1[CH2:8][CH2:4][CH2:3][CH:2]([O:1][C:57]2[S:56][N:19]=[CH:59][C:58]=2[NH:60][C:44]([C:32]2[N:33]=[C:34]([C:36]3[C:37]([F:43])=[CH:38][CH:39]=[CH:40][C:41]=3[F:42])[S:35][CH:31]=2)=[O:46])[CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 22933363tert-Butyl 4-hydroxyazepane-1-carboxylateHCID 242784542-(2,6-Difluorophenyl)-1,3-thiazole-4-carboxylic acidHCID 594556885-Amino-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid

Product 1

HCID 71261898N-(5-(azepan-4-yloxy)isothiazol-4-yl)-2-(2,6-difluorophenyl)thiazole-4-carboxamide

Procedure

Following the procedure described in Example 1, and substituting Compound 1B2 in Step (1) with tert-butyl 4-hydroxyazepane-1-carboxylate (2B2) (200 mg, 0.93 mmol) and Compound 1E in Step 4 with 2-(2,6-difluorophenyl)thiazole-4-carboxylic acid (2E) (40 mg, 0.166 mmol), the title compound 2 (35 mg, 0.080 mmol) was obtained.

Sources & evidence

ORD record
ord-3f51e867898040a0961bbe345059ed64
Source dataset
uspto-grants-2015_03
Patent number
US08969584B2

Reaction notes

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