Methyl N-(triethylammoniosulfonyl)carbamate → HCID 58456287, compound

HRID 410609Notes

Reaction equation

[CH:1]([NH:3][NH:4][C:5](=O)[C:6]([CH3:32])([CH3:31])[CH2:7][C:8]1[S:9][C:10]([C:13]2[CH:18]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=3)[CH:16]=[C:15]([CH3:30])[CH:14]=2)=[CH:11][N:12]=1)=[O:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:30][C:15]1[CH:16]=[C:17]([NH:19][C:20]2[N:25]=[C:24]([C:26]([F:27])([F:29])[F:28])[CH:23]=[CH:22][N:21]=2)[CH:18]=[C:13]([C:10]2[S:9][C:8]([CH2:7][C:6]([CH3:31])([C:5]3[O:2][CH:1]=[N:3][N:4]=3)[CH3:32])=[N:12][CH:11]=2)[CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product from Step 1 (70 mg, 0.146 mmol) was taken up in THF (2.0 mL) in a microwave vial, and Burgess reagent (70 mg, 0.293 mmol) was added. The reaction was heated in the microwave at 100° C. for 30 min. The orange reaction mixture was concentrated to dryness, and the resulting residue was purified by flash chromatography (10-100% ethyl acetate in hexanes) to provide N-(3-methyl-5-{2-[2-methyl-2-(1,3,4-oxadiazol-2-yl)propyl]-1,3-thiazol-5-yl}phenyl)-4-(trifluoromethyl)pyrimidin-2-amine (32 mg, 48%) as a colorless foam. MS ESI: [M+H]+ m/z 461.0. 1H NMR (600 MHz, DMSO-d6) δ 10.22 (s, 1H), 9.16 (s, 1H), 8.80 (d, J=4.9, 1H), 7.94-7.83 (m, 2H), 7.42 (s, 1H), 7.25 (d, J=4.9, 1H), 7.08 (s, 1H), 3.39 (s, 2H), 2.27 (s, 3H), 1.43 (s, 6H). rhSYK activity=+++

Workup

additionwas added
concentrationThe orange reaction mixture was concentrated to dryness
customthe resulting residue was purified by flash chromatography (10-100% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-a78a0fe369f748a1a0898e9d64f7ff47
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759366B2

Reaction notes

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