Dimethylformamide → 3-[3-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-1,1-dimethylurea

HRID 1926346Notes

Reaction equation

HRID 1926346 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.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24].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:23](=[O:24])[N:22]([CH3:26])[CH3:21])=[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 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 675208705-(3-Aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine

Product 1

HCID 675209823-[3-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-1,1-dimethylurea

Procedure

A mixture of 5-(3-aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine (10.0 mg, 0.0357 mmol), N,N-dimethylcarbamoyl chloride (3.60 uL, 0.0392 mmol), DMF (1 mL, 0.01 mol) and DIPEA (0.03 mL, 0.2 mmol) was stirred at rt for 30 min. 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=2.93 (s, 6H), 4.13-4.18 (m, 2H), 7.39-7.45 (m, 1H), 7.51 (td, J=7.7, 1.3 Hz, 1H), 7.96 (d, J=7.3 Hz, 1H), 8.01 (d, J=8.1 Hz, 1H), 8.09 (d, J=2.0 Hz, 1H), 8.14 (s, 1H). MS (ES+): m/z=352.11 (100) [MH+]. HPLC: tR=3.11 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-2b93cfdbf7bd429eb02a65bf3777b1d0
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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