Ammonium Chloride → HCID 86668125, compound

HRID 474290Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([NH:18][CH2:19][CH2:20][CH:21]([OH:39])[CH2:22][O:23][C:24]2[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][C:25]=2[N:33]2[CH:37]=[N:36][C:35]([CH3:38])=[N:34]2)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:30][C:28]1[CH:27]=[CH:26][C:25]([N:33]2[CH:37]=[N:36][C:35]([CH3:38])=[N:34]2)=[C:24]([CH:29]=1)[O:23][CH2:22][CH:21]([OH:39])[CH2:20][CH2:19][NH:18][C:4]1[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 4-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)-1-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butan-2-ol (70 mg, 0.126 mmol), iron (42.3 mg, 0.758 mmol) and ammonium chloride (67.6 mg, 1.264 mmol) in MeOH (842 μL) and water (421 μL) was heated at 80° C. for 1 h. The crude product was purified by Prep-HPLC to obtain 1-(5-amino-2-(3-methyl-1H-1,2,4-triazol-1-yl)phenoxy)-4-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)butan-2-ol (53 mg, 80% yield). LC-MS (M+H)+=524.3. 1H NMR (500 MHz, methanol-d4) δ 9.30 (s, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.23-7.15 (m, 2H), 7.10-7.04 (m, 2H), 6.98 (s, 1H), 6.84 (dd, J=8.9, 1.8 Hz, 1H), 4.38-4.32 (m, 1H), 4.24-4.20 (m, 1H), 4.19-4.07 (m, 2H), 3.77-3.67 (m, 2H), 2.88-2.80 (m, 1H), 2.76-2.70 (m, 2H), 2.50 (d, J=1.5 Hz, 3H), 2.09-2.03 (m, 1H), 2.01-1.94 (m, 1H), 1.87 (d, J=5.5 Hz, 1H).

Workup

customThe crude product was purified by Prep-HPLC

Sources & evidence

ORD record: ord-57825b96d7844fd79fc93b0548d77dc7
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637523B2

Reaction notes

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