Dimethylformamide → HCID 68007381, compound

HRID 527001Notes

Reaction equation

HRID 527001 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23]C[CH2:21][C@@H:20](NCCNC)[CH2:19]4)[C:14]([F:29])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH:30]([N:33](C(C)C)[CH2:34]C)(C)C.C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)OC1C=CC([N+]([O-])=O)=CC=1.[CH3:61][N:62]([CH:64]=[O:65])[CH3:63]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:19][CH2:20][CH2:21][C@@H:61]([N:62]5[CH2:63][CH2:30][N:33]([CH3:34])[C:64]5=[O:65])[CH2:23]4)[C:14]([F:29])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 78756Bis(4-nitrophenyl) carbonateHCID 81531DiisopropylethylamineHCID 68008586HCID 68008586, compound2×

Product 1

HCID 68007381HCID 68007381, compound

Procedure

In a flask containing (1S,3R)—N1-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)-N3-(2-(methylamino)ethyl)cyclohexane-1,3-diamine, 47c, (0.020 g, 0.048 mmol) in DMF was added diisopropylethylamine (0.025 mL, 0.144 mmol) and bis(4-nitrophenyl) carbonate (0.016 g, 0.053 mmol). The reaction mixture was stirred at room temperature for 3 hrs. The resulting residue was purified by HPLC using 5-70% MeOH/H2O with 6 mM HCl to provide the desired product.

Workup

  1. customThe resulting residue was purified by HPLC

Sources & evidence

ORD record
ord-cc7765615ec14e85b2d3c93d9ee5304a
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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