Ethanolamine → HCID 42606565, compound

HRID 222375Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18]3[S:19][C:20]([C:23](O)=[O:24])=[CH:21][N:22]=3)=[O:16])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:26][CH2:27][CH2:28][OH:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18]3[S:19][C:20]([C:23]([NH:26][CH2:27][CH2:28][OH:29])=[O:24])=[CH:21][N:22]=3)=[O:16])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-[({1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-thiazole-5-carboxylic acid (Intermediate 14) (0.18 g, 0.45 mmol), 2-aminoethanol (32 μL, 1.2 eq), HATU (0.22 g, 1.3 eq) and DIPEA (100 μL, 1.3 eq) in DMF (20 mL) was stirred at 40° C. for 48 hours. The solvent was evaporated and the residue was washed with water and extracted with DCM. The insoluble compound was filtered and washed with a mixture of acetonitrile/methanol 80/20 and then purified by flash chromatography eluting with DCM/MeOH (95/5) to give the title compound as a white solid (60 mg, 30%). HRMS calculated for C16H14Cl2N6O3S (M+H)+441.0303, found: 441.0339, Rt: 2.39 min. MP: 274.8° C.

Workup

customThe solvent was evaporated
washthe residue was washed with water
extractionextracted with DCM
filtrationThe insoluble compound was filtered
washwashed with a mixture of acetonitrile/methanol 80/20
custompurified by flash chromatography
washeluting with DCM/MeOH (95/5)

Sources & evidence

ORD record: ord-cff75d404a2f4cb9be46616ae4ec1340
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207204B2

Reaction notes

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