O-Phenylenediamine → HCID 22478729, compound

HRID 252784Notes

Reaction equation

HRID 252784 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=3)=[CH:8][C:6]=2[N:7]=1.[C:23]1([NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C>[NH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:30][C:18](=[O:20])[C:17]1[CH:16]=[CH:15][C:14]([CH2:13][NH:12][C:9]2[CH:10]=[CH:11][C:5]3[S:4][C:3]([NH:2][CH3:1])=[N:7][C:6]=3[CH:8]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22478646HCID 22478646, compound

Product 1

HCID 22478729HCID 22478729, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of acid 456c (729 mg; 2.54 mmol), 1,2-phenylenediamine (376 mg; 3.47 mmol; 1.36 eq) and BOP (1.43 g; 3.23 mmol; 1.27 eq) was dissolved in acetonitrile (15 mL), treated with triethylamine (3 mL) and stirred overnight. The reaction mixture was quenched with methanol, concentrated and purified by chromatographic column on silica gel (40% EtOAc in DCM) and the obtained material crystallized from DCM to give 358 mg (0.88 mmol; 35% yield) of pure compound 456. 1H-NMR (300 MHz; DMSO-d6) δ (ppm): 9.57 (s, 1H), 7.92 (d, J=7.9 Hz, 2H), 7.66 (d, J=4.8 Hz, 1H), 7.48 (d, J=8.3 Hz, 2H), 7.26 (d, J=8.3 Hz, 1H), 7.15 (d, J=7.9 Hz, 1H), 6.95 (t, J=7.5 Hz, 1H), 6.76 4.87 (bs, 2H), 6.58 (t, J=7.5 Hz, 1H), 6.54 (d, J=1.8 Hz, 1H), 6.13 (dd, J=1.8, 8.3 Hz, 1H), 6.27 (t, J=5.7 Hz, 1H), 4.87 (bs, 2H), 4.36 (d, J=5.7 Hz, 2H), 2.85 (d, J=4.8 Hz, 3H). LRMS: calc: 403.5008. found: 404.2 (M+NH) and 202.6 (M+2H)/2.

Workup

  1. customThe reaction mixture was quenched with methanol
  2. concentrationconcentrated
  3. custompurified by chromatographic column on silica gel (40% EtOAc in DCM)
  4. customthe obtained material crystallized from DCM

Sources & evidence

ORD record
ord-b476a3598772426e8e79e52697e7408c
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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