Ammonia methanol → 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide

HRID 575117Notes

Reaction equation

HRID 575117 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]2[C:8](=[O:25])[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.[NH3:26].CO>C1COCC1>[OH:24][C:21]([CH3:23])([CH3:22])[C:20]#[C:19][C:16]1[CH:17]=[CH:18][C:11]2[O:10][CH2:9][C:8](=[O:25])[C:7]3[S:6][C:5]([C:3]([NH2:26])=[O:2])=[N:14][C:13]=3[C:12]=2[CH:15]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 866931459-(3-Hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester

Product 1

HCID 717147149-(3-Hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (81 mg, 0.23 mmol) in THF (4 mL) at room temperature, NH3/CH3OH (self-made, 4 mL) was added. The mixture was stirred at room temperature for 3 h, then concentrated to give 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide as a yellow oil, which was used in the next step without any further purification (crude, 80 mg). 1H NMR (400 MHz, DMSO-d6): δ 830 (s, 1H), 8.43 (d, J=2.1 Hz, 1H), 8.18 (s, 1H), 7.50 (dd, J1=8.4 Hz, J2=2.2 Hz, 1H), 7.26 (d, J=8.4 Hz, 1H), 5.48 (s, 1H), 4.87 (s, 2H), 1.47 (s, 6H); LC-MS (ESI & APCI): 343.2 (M+1).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-b100dc3de8774704b2835aa7a15b0fae
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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