HOAt → HCID 86664395, compound

HRID 1626490Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:22]([O:24][CH2:25][CH3:26])=[O:23].[NH2:27][C:28]1[S:29][CH:30]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[N:32]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1>CC(N(C)C)=O.C(OCC)(=O)C>[C:33]([C:31]1[N:32]=[C:28]([NH:27][C:17]([C:16]2[CH:20]=[CH:21][C:13]([O:12][C:11]3[CH:10]=[C:9]4[C:4]([CH:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:6][CH2:7][O:8]4)=[CH:3][C:2]=3[Cl:1])=[CH:14][CH:15]=2)=[O:18])[S:29][CH:30]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

Conditions

Temperature: 50 °C

Procedure

4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (53 mg, 0.141 mmol) and 2-amino-4-tert-butylthiazole (44.0 mg, 0.281 mmol) in DMA were treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53.9 mg, 0.281 mmol) followed by 1-hydroxy-7-azabenzotriazole (19.1 mg, 0.141 mmol) at ambient temperature. The reaction was heated to 50° C. for 14 hours. The reaction was diluted with ethyl acetate, washed with 1 N HCl, saturated aqueous bicarbonate, and brine. The ethyl acetate layer was dried with sodium sulfate and the product purified on SP1 (20 to 65% Ethyl acetate/hexane) to provide the desired compound (47 mg).

Workup

washwashed with 1 N HCl, saturated aqueous bicarbonate, and brine
dry with materialThe ethyl acetate layer was dried with sodium sulfate
customthe product purified on SP1 (20 to 65% Ethyl acetate/hexane)

Sources & evidence

ORD record: ord-21d4756bfd88447cba894a82fa8d7362
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785445B2

Reaction notes

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