Ammonia methanol → 4-Acetylamino-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide
Reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]2[CH:8]([NH:25][C:26](=[O:28])[CH3:27])[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]([OH:24])([CH3:23])[CH3:22])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=O.CO.[NH3:31]>>[C:26]([NH:25][CH:8]1[C:7]2[S:6][C:5]([C:3]([NH2:31])=[O:2])=[N:14][C:13]=2[C:12]2[CH:15]=[C:16]([C:19]#[C:20][C:21]([OH:24])([CH3:22])[CH3:23])[CH:17]=[CH:18][C:11]=2[O:10][CH2:9]1)(=[O:28])[CH3:27]Participants
Reactant 2
Product 1
Procedure
A solution of 4-Acetylamino-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (81 mg, 0.202 mmol), in methanol-ammonia (5 mL) was stirred at room temperature for 0.5 h. The reaction mixture was concentrated to afford crude product, which was triturated with EtOAc and hexane (1:1) and then filtered to afford compound 4-Acetylamino-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (36 mg, 47%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.74 (d, J=8.5 Hz, 1H), 8.6 (d, J=2.2 Hz, 1H), 8.49 (s, 1H), 7.92 (s, 1H), 7.34 (dd, J1=8.3 Hz, J2=2.2 Hz, 1H), 7.10 (d, J=8.4 Hz, 2H), 5.53 (m, 1H), 5.45 (s, 1H), 4.37 (m, 1H), 4.18 (m, 1H), 1.89 (s, 3H), 1.49 (s, 6H); LC-MS (ESI & APCI): 386.5 (M+1).
Workup
- concentrationThe reaction mixture was concentrated
- customto afford crude product, which
- customwas triturated with EtOAc and hexane (1:1)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-e15f7e44c7164f16a22f6e4e6dda9342
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
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