N,N-Dimethylglycine → N-[3-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-2-dimethylaminoacetamide
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]([CH2:24][C:25](O)=[O:26])[CH3:23].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.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:25](=[O:26])[CH2:24][N:22]([CH3:23])[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]=1Participants
6
Reactant 5
Product 1
Procedure
A mixture of 5-(3-aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine (10.0 mg, 0.0357 mmol), dimethylaminoacetic acid (4.05 mg, 0.0392 mmol), TBTU (17.2 mg, 0.0535 mmol), DMF (1 mL, 0.01 mol) and DIPEA (0.03 mL, 0.0002 mol) 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=2.66 (br. s., 6H), 3.54 (br. s., 2H), 4.28 (s, 2H), 7.42-7.47 (m, 1H), 7.53 (td, J=7.7, 1.3 Hz, 1H), 7.99 (d, J=7.3 Hz, 1H), 8.03 (d, J=7.6 Hz, 1H), 8.09 (d, J=2.0 Hz, 1H), 8.15 (d, J=1.8 Hz, 1H). MS (ES+): m/z=366.13 (100) [MH+]. HPLC: tR=2.43 min (ZQ3, polar—5 min).
Workup
- customThe solution was used directly for HPLC purification
- additionThe fractions containing the pure product
- concentrationwere concentrated in vacuo
Sources & evidence
- ORD record
- ord-5a591c8b91a3440ab81fa9d12e07e250
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178668B2
Reaction notes
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