Hydrochloric Acid → HCID 9800108, compound

HRID 1934427Notes

Reaction equation

C[O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[C:7]2[C:14]([C:15](=[O:19])[C:16]([NH2:18])=[O:17])=[C:13]([CH2:20][CH3:21])[N:12]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:8]=2[N:9]=[CH:10][N:11]=1.[OH-].[Na+].Cl>CO>[NH2:18][C:16](=[O:17])[C:15]([C:14]1[C:7]2[C:6]([O:5][CH2:4][C:3]([OH:29])=[O:2])=[N:11][CH:10]=[N:9][C:8]=2[N:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13]=1[CH2:20][CH3:21])=[O:19]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 215 mg (0.542 mmol) of [[5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 3 mL of methanol were treated with 0.406 mL of 2 M sodium hydroxide and heated to 55° C. for 3 hours. The reaction was cooled to ambient temperature, 1.0 mL of 1 M HCl was added and the resulting slurry was concentrated under vacuum. The crude solid was combined with 20 mL of water and stirred for 20 minutes. The precipitate was collected by filtration, washed with 20 mL of water, and dried in vacuo (40° C., 10 torr) to provide 190 mg (91.7%) of [[5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid. as a white solid. nmr (500 MHz, dmso-d6) δ1.01 (t, J=7.4 Hz, 3H), 2.95 (q, J=7.4 Hz, 2H), 4.93 (s, 2H), 5.60 (s, 2H), 7.13 (d, J=7.2 Hz, 2H), 7.31 (m, 3H), 7.56 (s, 1H), 7.98 (s, 1H), 8.46 (s, 1H) 12.99 (bs, 1H)

Workup

temperatureThe reaction was cooled to ambient temperature
concentrationthe resulting slurry was concentrated under vacuum
filtrationThe precipitate was collected by filtration
washwashed with 20 mL of water
customdried in vacuo (40° C., 10 torr)

Sources & evidence

ORD record: ord-85159620c62a47b482ce8a14fa16352c
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384041B1

Reaction notes

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