Hydrochloric Acid → HCID 86697398, compound

HRID 237727Notes

Reaction equation

C[O:2][C:3](=[O:32])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([C:25]5[C:26](F)=[N:27][CH:28]=[CH:29][CH:30]=5)[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.[OH-].[Na+].Cl>CN1CCCC1=O>[F:24][C:22]1[CH:21]=[CH:20][C:19]([C:25]2[C:26]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[N:27][CH:28]=[CH:29][CH:30]=2)=[C:18]2[C:23]=1[C@H:15]([O:14][C:12]1[CH:11]=[CH:10][C:9]3[C@H:5]([CH2:4][C:3]([OH:32])=[O:2])[CH2:6][O:7][C:8]=3[CH:13]=1)[CH2:16][CH2:17]2

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of {(S)-6-[(R)-7-fluoro-4-(2-fluoro-pyridin-3-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.10 g), morpholine (0.10 g) and N-methyl-pyrrolidone (2 mL) is stirred at 180° C. for 48 h. After cooling to room temperature, 2 N aqueous NaOH solution (0.5 mL) is added, and the resulting mixture is stirred at 40° C. for 2 h. The mixture is neutralized with 1 N aqueous HCl solution and concentrated. The residue is chromatographed on reversed phase (HPLC; acetonitrile/water) to give the title compound. LC (method 7): tR=0.89 min; Mass spectrum (ESI+): m/z=491 [M+H]+.

Workup

temperatureAfter cooling to room temperature
stirringthe resulting mixture is stirred at 40° C. for 2 h
concentrationconcentrated
customThe residue is chromatographed on reversed phase (HPLC; acetonitrile/water)

Sources & evidence

ORD record: ord-4a23731d270e4b2681d5f4d6dba157c5
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642585B2

Reaction notes

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