Water → 5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-vinylpyrimidin-2-yl)thiophene-2-sulfonamide

HRID 1484940Notes

Reaction equation

HRID 1484940 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH:26]4[CH2:28][CH2:27]4)[NH:23][N:22]=3)[C:17]([CH:29]=[CH2:30])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.B(Cl)(Cl)Cl.O>C(Cl)Cl>[CH:26]1([C:24]2[NH:23][N:22]=[C:21]([NH:20][C:18]3[C:17]([CH:29]=[CH2:30])=[CH:16][N:15]=[C:14]([C:11]4[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=4)[N:19]=3)[CH:25]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 962WaterHCID 25135Boron TrichlorideHCID 58169328N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-vinylpyrimidin-2-yl)thiophene-2-sulfonamide

Product 1

HCID 509437755-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-vinylpyrimidin-2-yl)thiophene-2-sulfonamideYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-vinylpyrimidin-2-yl)thiophene-2-sulfonamide (80 mg, 0.17 mmol) and BCl3 (3 mL) in DCM (10 mL) was stirred for 0.5 h, Water was added and extracted with EA. The combined organic layers were dried (NaHSO4), filtered. The filtrate was concentrated to afford the compound 5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-vinylpyrimidin-2-yl)thiophene-2-sulfonamide (Compound 209) (70 mg, 90%). LC-MS (m/z)=389 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 0.80-0.81 (m, 2H), 1.01-1.04 (m, 2H), 1.96-2.02 (m, 1H), 5.50 (d, J=11.6 Hz, 1H), 5.96 (d, J=17.2 Hz, 1H), 6.43 (s, 1H), 7.08-7.15 (m, 1H), 7.63 (d, J=4 Hz, 1H), 7.87 (bs, 2H), 8.00 (bs, 1H), 8.56 (s, 1H), 10.13 (bs, 1H).

Workup

  1. extractionextracted with EA
  2. dry with materialThe combined organic layers were dried (NaHSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4bfe9691a09c4aa8866f16d60d4ab3c3
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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