tert-butyl 2-amino-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate → HCID 59522556, compound

HRID 388936Notes

Reaction equation

HRID 388936 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([NH2:17])[S:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-]=C=S.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH:30][C:31]([C:33]3[CH:50]=[CH:49][C:36]4[N:37]=[C:38](NC5N(C(C)C)C=CN=5)[NH:39][C:35]=4[CH:34]=3)=[O:32])[CH:28]=2)[CH:23]=[N:22]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([NH:17][C:38]3[NH:39][C:35]4[CH:34]=[C:33]([C:31](=[O:32])[NH:30][C:27]5[CH:28]=[C:29]6[C:24]([CH:23]=[N:22][NH:21]6)=[CH:25][CH:26]=5)[CH:50]=[CH:49][C:36]=4[N:37]=3)[S:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 11357283tert-butyl 2-amino-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylateHCID 59522617HCID 59522617, compoundHCID 178418790HCID 178418790, compound

Product 1

HCID 59522556HCID 59522556, compound

Procedure

The amine (0.5 mmol) from above was converted to corresponding isothiocyanate using general procedure A, which was then reacted with 3,4-diamino-N-(1H-indazol-6-yl)-benzamide (0.5 mmol; see Example 25) according to general procedure B to yield 2-[6-(1H-indazol-6-ylcarbamoyl)-1H-benzimidazol-2-ylamino]-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester. MS: m/z 531 (M+H)+.

Sources & evidence

ORD record
ord-9ef8a56188c646c3a871c38f4f1ffc1e
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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