Ammonia → HCID 67008552, compound

HRID 1672427Notes

Reaction equation

Cl[C:2]1[C:3]([N:8]2[CH2:13][CH:12]=[C:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:19][CH:18]=3)=[O:15])[C@@H:10]([CH3:30])[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.N.[CH3:32]O>>[CH3:30][C@@H:10]1[C:11]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[O:15])=[CH:12][CH2:13][N:8]([C:3]2[C:2]([CH3:32])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol

HCID 67007780HCID 67007780, compound

Product 1

HCID 67008552HCID 67008552, compoundYield 54%

Procedure

The title compound (51 mg, 54%) was prepared using similar procedure as described in Example 3, substituting the product from Example 5 for the product from Example 1G. 1H NMR (300 MHz, CDCl3) δ 8.19-8.17 (m, 1H), 8.00 (d, 2H, J=9.2 Hz), 7.90 (d, 2H, J=9.2 Hz), 7.86 (br s, 1H), 7.47-7.43 (m, 1H), 6.91 (dd, 1H, J=7.1, 4.8 Hz), 6.68 (dd, 1H, J=3.4, 3.4 Hz), 3.94 (app t, 2H, J=2.4 Hz), 3.23 (app d, 2H, J=4.1 Hz), 3.10-2.99 (m, 1H), 2.35 (s, 3H), 1.27 (d, 3H, J=7.1 Hz); MS (DCI/NH3) m/e 440 (M+H)+; [α]23D −38.0° (c 0.25, CH3OH).

Sources & evidence

ORD record: ord-ce04e485a4eb4b89bf855ffad7662818
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998982B2

Reaction notes

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