Dimethylformamide → [3-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-urea

HRID 1926347Notes

Reaction equation

HRID 1926347 reaction equation
[NH2:1][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]([C:12]2[S:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[C:8]([NH2:11])=[N:9][CH:10]=1.C[Si]([N:25]=[C:26]=[O:27])(C)C.CN(C=O)C.CCN(C(C)C)C(C)C>>[NH2:11][C:8]1[N:9]=[CH:10][C:5]([C:4]#[C:3][CH2:2][NH:1][C:26]([NH2:25])=[O:27])=[CH:6][C:7]=1[C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 675208705-(3-Aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine

Product 1

HCID 67521056[3-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-urea

Procedure

A mixture of 5-(3-aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine (10.0 mg, 0.0357 mmol), trimethylsilyl isocyanate (5.31 uL, 0.0392 mmol), DMF (1 mL, 0.01 mol) and DIPEA (0.03 mL, 0.2 mmol) was stirred at rt for 3 h. The solution was used directly for HPLC purification. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=4.14 (s, 2H), 7.39-7.45 (m, 1H), 7.47-7.52 (m, 1H), 7.93 (s, 1H), 8.00 (d, J=7.8 Hz, 1H), 8.06 (d, J=2.0 Hz, 1H). MS (ES+): m/z=324.10 (100) [MH+]. HPLC: tR=2.85 min (ZQ3, polar—5 min).

Workup

  1. customThe solution was used directly for HPLC purification
  2. additionThe fractions containing the pure product
  3. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-ccc4029e4f204e2a8cc8fb19c3cfa28b
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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