1,3-Propanediamine → HCID 23729154, compound

HRID 2080294Notes

Reaction equation

HRID 2080294 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][NH:9][C:10](=[O:35])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[N:13][C:12]=2[NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:36]([NH2:40])[CH2:37][CH2:38][NH2:39]>CN1C(=O)CCC1>[NH2:39][CH2:38][CH2:37][CH2:36][NH:40][C:2]1[N:7]=[C:6]([CH2:8][NH:9][C:10](=[O:35])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[N:13][C:12]=2[NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 57542305HCID 57542305, compound

Product 1

HCID 23729154HCID 23729154, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of N-((6-bromopyridin-2-yl)methyl)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide (50 mg, 0.095 mmol) and propane-1,3-diamine (396 ul, 4.75 mmol) in NMP was stirred in microwave at 15° C. for 15 min. The reaction mixture was purified on RP-HPLC using a mixture of acetonitrile and H2O gave N-((6-(3-aminopropylamino)pyridin-2-yl)methyl)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide (28 mg, 56%). LRMS (M+H+) m/z 524.1.

Workup

  1. customThe reaction mixture was purified on RP-HPLC
  2. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-2c7a5e3ecf1c4c54a1a0812ba62a76f3
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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