Diisopropylethylamine → HCID 58709775, compound

HRID 2375843Notes

Reaction equation

HRID 2375843 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH2:21][CH2:22][N:23]([C:26]([C:28]6([CH2:31]O)[CH2:30][CH2:29]6)=[O:27])[CH2:24][CH:25]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([N:36]([CH2:40][CH3:41])[CH:37]([CH3:39])C)(C)C.[CH3:42]S(OS(C)(=O)=O)(=O)=O>CN(C)C=O>[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH2:21][CH2:22][N:23]([C:26]([C:28]6([CH2:31][N:36]7[CH2:37][CH2:39][CH2:42][CH2:41][CH2:40]7)[CH2:29][CH2:30]6)=[O:27])[CH2:24][CH:25]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 58709814HCID 58709814, compound

Product 1

HCID 58709775HCID 58709775, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {4-[4-(benzothiazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridin-1-yl}-(1-hydroxymethylcyclopropyl)-methanone (23.0 mg, 0.05 mmol) in N,N-dimethylformamide (1 mL) were added N,N-diisopropylethylamine (0.05 mL, 0.3 mmol) and methanesulfonic anhydride (11 mg, 0.06 mmol). The resulting mixture was stirred at rt overnight. LC-MS showed the reaction produced the desired product, but there was still 70% SM, another 1.2 eq. of methanesulfonic anhydride was added. 2 h later, LC-MS showed the reaction was complete. To the reaction mixture was added piperidine (0.05 mL, 0.5 mmol), and the resulting mixture was stirred at rt overnight. LC-MS showed the reaction was complete. The mixture was diluted with MeOH (1 mL) and purified by mass-directed purification to give the title compounds as an off-white solid. LC-MS (ES, Pos.): 514 [MH+]. 1H NMR (CD3OD, 400 MHz): δ=0.76 (s, 2H), 0.99 (s, 2H), 1.41-1.54 (m, 6H), 2.42-2.69 (m, 8H), 3.99 (m, 2H), 4.23 (m, 1H), 4.50 (m, 1H), 6.35 (s, 1H), 6.73 (s, 1H), 7.78 (dd, J=8.9 Hz, 2.1 Hz, 1H), 8.01 (d, J=8.9 Hz, 1H), 8.29 (s, 1H), 8.74 (d, J=2.1 Hz, 1H), 9.12 (s, 1H).

Sources & evidence

ORD record
ord-5be43bf26720406eb435a5dfcca7eb58
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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