Hydrochloric Acid → HCID 58222961, compound

HRID 2093756Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:49]=[CH:48][C:12]([CH2:13][NH:14][C:15]2[N:20]=[C:19]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[N:18]=[C:17]([NH:27][C:28]3[CH:47]=[CH:46][C:31]([C:32]([NH:34][CH:35]([CH:40]4[CH2:45][CH2:44][CH2:43][NH:42][CH2:41]4)[C:36]([O:38]C)=[O:37])=[O:33])=[CH:30][CH:29]=3)[N:16]=2)=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+].O.Cl>CC(C)=O>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH:14][C:15]2[N:20]=[C:19]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[N:18]=[C:17]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH:34][CH:35]([CH:40]4[CH2:45][CH2:44][CH2:43][NH:42][CH2:41]4)[C:36]([OH:38])=[O:37])=[O:33])=[CH:46][CH:47]=3)[N:16]=2)=[CH:48][CH:49]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of methyl 2-(4-(4-(4-(6-aminohexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)-2-(piperidin-3-yl)acetate (50 mg) and K2CO3 (50.2 mg) in acetone (2 mL)/water (2 mL) was heated at 85° C. for 4 hours. After cooling to room temperature, the mixture was acidified with 1N HCl to pH=3. All the solvents were removed under vacuum. The residue was purified by preparative HPLC to give 2-(4-(4-(4-(6-aminohexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)-2-(piperidin-3-yl)acetic acid (40 mg).

Workup

temperatureAfter cooling to room temperature
customAll the solvents were removed under vacuum
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-d46a05f7a41442fdaa7643e0c1b16d0f
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445490B2

Reaction notes

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