Methyl N-(triethylammoniosulfonyl)carbamate → HCID 58456391, compound

HRID 410619Notes

Reaction equation

[CH:1]([NH:3][NH:4][C:5]([C:7]1([C:10]2[S:11][C:12]([C:15]3[CH:20]=[C:19]([NH:21][C:22]4[N:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][N:23]=4)[CH:18]=[C:17]([CH3:32])[CH:16]=3)=[CH:13][N:14]=2)[CH2:9][CH2:8]1)=O)=[O:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:32][C:17]1[CH:18]=[C:19]([NH:21][C:22]2[N:27]=[C:26]([C:28]([F:30])([F:31])[F:29])[CH:25]=[CH:24][N:23]=2)[CH:20]=[C:15]([C:12]2[S:11][C:10]([C:7]3([C:5]4[O:2][CH:1]=[N:3][N:4]=4)[CH2:8][CH2:9]3)=[N:14][CH:13]=2)[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product from Step 1 (85 mg, 0.184 mmol) was taken up in THF (2 mL) in a microwave vial, and Burgess reagent (88 mg, 0.368 mmol) was added. The reaction was heated in the microwave at 100° C. for 30 min. The yellow reaction mixture was concentrated to dryness, and the resulting residue was purified by flash chromatography (25-100% ethyl acetate in hexanes) to afford N-(3-methyl-5-{2-[1-(1,3,4-oxadiazol-2-yl)cyclopropyl]-1,3-thiazol-5-yl}phenyl)-4-(trifluoromethyl)pyrimidin-2-amine (18 mg, 22%) as a colorless solid. MS ESI: [M+H]+ m/z 445.0. 1H NMR (600 MHz, DMSO-d6) δ 10.23 (s, 1H), 9.23 (s, 1H), 8.81 (d, J=4.9, 1H), 7.97 (s, 1H), 7.96 (s, 1H), 7.46 (s, 1H), 7.26 (d, J=4.9, 1H), 7.15 (s, 1H), 2.29 (s, 3H), 1.94-1.82 (m, 4H). rhSYK activity=+++

Workup

additionwas added
concentrationThe yellow reaction mixture was concentrated to dryness
customthe resulting residue was purified by flash chromatography (25-100% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-5c74b524308140f4979f8c7b8de5ccb2
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759366B2

Reaction notes

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