2-Aminothiazole → HCID 87417779, compound

HRID 2103617Notes

Reaction equation

[CH:1]1([CH:6]2[CH2:8][C:7]2([C:12]2[S:13][C:14]([S:17](=[O:24])(=[O:23])/[N:18]=[CH:19]\[N:20]([CH3:22])[CH3:21])=[CH:15][CH:16]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>>[S:27]1[CH:28]=[CH:29][N:30]=[C:26]1[NH:25][C:9]([C:7]1([C:12]2[S:13][C:14]([S:17](=[O:23])(=[O:24])/[N:18]=[CH:19]\[N:20]([CH3:21])[CH3:22])=[CH:15][CH:16]=2)[CH2:8][CH:6]1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)=[O:11]

Participants

Reactant 4

HCID 21552-Aminothiazole

HCID 8471Triethylamine

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

HCID 87417623HCID 87417623, compound

Product 1

HCID 87417779HCID 87417779, compoundYield 50.5%

Procedure

According to method 16h was used (±)-(Z)-2-cyclopentyl-1-[5-(dimethylaminomethylene-sulfamoyl)-thiophen-2-yl]-cyclopropanecarboxylic acid (65 mg, max. 0.344 mmol), 2-amino-thiazole (19 mg, 0.188 mmol), TBTU (60 mg, 0.188 mmol) and triethylamine (57 μL, 0.402 mmol) to give 43 mg of purified product. MS (m/e): 453.0 (M+H).

Sources & evidence

ORD record: ord-da9c1df18b464adf9a74bf0b98997ba2
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576108B2

Reaction notes

Loading…