Ammonium Chloride → HCID 57563005, compound

HRID 1726285Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH:17]2[CH2:22][CH2:21][N:20]([C@H:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27]([C:29]3[C:30]([CH3:36])=[N:31][CH:32]=[N:33][C:34]=3[CH3:35])=[O:28])[CH2:19][CH2:18]2)[CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)=[CH:6][CH:5]=1.[Cl-].[NH4+:40]>>[C:3]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:17]2[CH2:22][CH2:21][N:20]([C@H:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27]([C:29]3[C:30]([CH3:36])=[N:31][CH:32]=[N:33][C:34]=3[CH3:35])=[O:28])[CH2:19][CH2:18]2)=[CH:6][CH:5]=1)(=[O:2])[NH2:40]

Participants

Reactant 2

HCID 25517Ammonium Chloride

HCID 57563074HCID 57563074, compound

Product 1

HCID 57563005HCID 57563005, compoundYield 36.7%

Procedure

Using general procedure K with COMPOUND 299 (61 mg, 0.11 mmol) followed by general procedure E with the resulting acid and ammonium chloride (10 mg, 0.18 mmol) afforded COMPOUND 300 as a pale yellow foam (21 mg, 35%, over 2 steps). 1H NMR (CDCl3) δ 1.03 (d, 3H, J=6.0 Hz), 1.15-1.25 (m, 1H), 1.54-1.58 (m, 2H), 1.78 (d, 3H, J=9.0 Hz), 2.20-2.23 (m, 1H), 2.53 (s, 6H), 2.60 (td, 1H, J=9.0, 3.0 Hz), 2.86-2.96 (m, 3H), 3.33 (td, 1H, J=9.0, 3.0 Hz), 3.69 (td, 1H, J=9.0, 3.0 Hz), 3.84-3.86 (m, 1H), 3.94 (s, 2H), 6.62 (d, 2H, J=9.0 Hz), 6.99-7.02 (m, 2H), 7.31 (dd, 1H, J=6.0, 3.0 Hz), 7.63 (d, 2H, J=9.0 Hz), 8.68 (d, 1H, J=3.0 Hz), 8.91 (s, 1H). ES-MS m/z 521 [M+H]+.

Sources & evidence

ORD record: ord-1137d4eee5d7413fa6174df3e5d599ca
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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