Ammonia methanol → 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-morpholin-4-yl-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]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[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.[NH3:33]>>[OH:24][C:21]([CH3:22])([CH3:23])[C:20]#[C:19][C:16]1[CH:17]=[CH:18][C:11]2[O:10][CH2:9][CH:8]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:7]3[S:6][C:5]([C:3]([NH2:33])=[O:2])=[N:14][C:13]=3[C:12]=2[CH:15]=1Participants
Reactant 2
Product 1
Procedure
A solution of 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-morpholin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (130 mg, 0.30 mmol) in methanol-ammonia (5 mL) was stirred at room temperature for 0.5 h. Then the reaction mixture was concentrated to afford crude compound which was triturated with EtOAc to afford compound 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-morpholin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (80 mg, 64%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.51 (d, J=1.88 Hz, 1H), 8.41 (s, 1H), 7.86 (s, 1H), 7.27 (dd, J1=8.4 Hz, J2=1.92 Hz, 1H), 7.02 (d, J=8.32 Hz, 1H), 5.43 (s, 1H), 4.40 (m, 3H), 3.54 (m, 4H), 2.65 (m, 4H), 1.46 (s, 6H); LC-MS (ESI & APCI): 414.6 (M+1).
Workup
- concentrationThen the reaction mixture was concentrated
- customto afford crude compound which
- customwas triturated with EtOAc
Sources & evidence
- ORD record
- ord-fa59a942983247e1a6c2cb98bb05e8dc
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
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