Methylamine → HCID 178485270, compound

HRID 510962Notes

Reaction equation

HRID 510962 reaction equation
CN.C1COCC1.[Cl:8][C:9]1[C:10]([CH3:38])=[C:11]([C:29]2[CH:30]=[C:31]([C:35]([OH:37])=O)[N:32]([CH3:34])[CH:33]=2)[C:12]([O:27][CH3:28])=[C:13]([CH:15]([NH:17][C:18]2[N:26]=[CH:25][N:24]=[C:23]3[C:19]=2[N:20]=[CH:21][NH:22]3)[CH3:16])[CH:14]=1.F[P-](F)(F)(F)(F)F.[N:46]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:50]2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[Cl:8][C:9]1[C:10]([CH3:38])=[C:11]([C:29]2[CH:30]=[C:31]([C:35]([NH:46][CH3:50])=[O:37])[N:32]([CH3:34])[CH:33]=2)[C:12]([O:27][CH3:28])=[C:13]([CH:15]([NH:17][C:18]2[N:26]=[CH:25][N:24]=[C:23]3[C:19]=2[N:20]=[CH:21][NH:22]3)[CH3:16])[CH:14]=1

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178492185HCID 178492185, compound

Product 1

HCID 178485270HCID 178485270, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 M Methylamine in THF (0.2 mL, 0.4 mmol) was added to a solution of 4-{3-chloro-6-methoxy-2-methyl-5-[1-(9H-purin-6-ylamino)ethyl]phenyl}-1-methyl-1H-pyrrole-2-carboxylic acid (10.0 mg, 0.02 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (24 mg, 0.054 mmol) in DMF (0.8 mL) at room temperature followed by addition of triethylamine (33 μL, 0.24 mmol). The reaction was stirred for 2 hours. The mixture was purified on RP-HPLC (XBridge C18 Column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product. LCMS calculated for C22H25ClN7O2 (M+H)+: m/z=454.2. found: 454.2.

Workup

  1. customThe mixture was purified on RP-HPLC (XBridge C18 Column
  2. washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-a99394d7f219404389a7a98320c29b3c
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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