2-Bromoethanol → HCID 25242541, compound

HRID 908496Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2-Bromoethanol (0.051 ml) was added to a stirred suspension of 3-(1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-piperidin-4-ylpyrazol-4-yl]pyridin-2-amine] (145 mg) and potassium carbonate (124 mg) in DMF (2 ml) at 100° C. The mixture was stirred at 100° C. for 15 hours. The reaction mixture was then purified by preparative HPLC using a Waters OBD reverse-phase column (C-18, 5 microns silica, 30 mm diameter, 150 mm length, flow rate of 40 ml/minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent to afford the title compound as (90 mg) as a solid.

Workup

customThe reaction mixture was then purified by preparative HPLC

Sources & evidence

ORD record: ord-69f61228c04c47a78cdc68f1e58aef1f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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