Phenylacetic Acid → HCID 11515518, compound

HRID 2108731Notes

Reaction equation

[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[N:11]=[C:12]([NH2:15])[S:13][CH:14]=2)=[CH:2]1.[C:16]1([CH2:22][C:23](O)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C1COCC1>[C:16]1([CH2:22][C:23]([NH:15][C:12]2[S:13][CH:14]=[C:10]([C:3]3[C:4]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[NH:1][CH:2]=3)[N:11]=2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 160 °C

Procedure

4-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine (216 mg, 1.0 mmol), phenylacetic acid (150 mg, 1.10 mmol) and N-(1-methanesulfonyl)benzotriazole (220 mg, 1.10 mmol) were placed in a microwave reaction vessel (Personal Chemistry, Uppsala, Sweden). THF (2 mL) was added followed by triethylamine (0.5 mL, 3.59 mmol) and the mixture heated in the sealed tube at 160° C. for 10 minutes. Upon cooling to room temperature the reaction was concentrated to 1 mL, and then acetonitrile was added (4 mL) and the product 2-Phenyl-N-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-acetamide precipitated, was filtered, washed with acetonitrile and dried. (150 mg, 45%). 1H NMR (500 MHz, DMSO-d6) 12.39 (1H, s), 11.83 (s,1H), 8.50 (1H, d, J=7.91 Hz), 8.27 (m,1H), 7.84 (1H, d, J=2.48 Hz), 7.36-7.15 (7H, m), 3.81 (2H, s). LC-MS Rt=2.8 min, [M+H]+=335.0, [M−H]−=333.1.

Workup

temperatureUpon cooling to room temperature the reaction
concentrationwas concentrated to 1 mL
additionacetonitrile was added (4 mL)
customthe product 2-Phenyl-N-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-acetamide precipitated
filtrationwas filtered
washwashed with acetonitrile
customdried

Sources & evidence

ORD record: ord-b28de9bb813149d8adaf416150726336
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514448B2

Reaction notes

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