Sodium Hydroxide → HCID 57731467, compound

HRID 2234693Notes

Reaction equation

HRID 2234693 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.[CH3:25][O:26][C:27]([NH:29][C:30]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[C:41]3[C:47]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=4[O:54][CH3:55])=[CH:46][N:45](S(C4C=CC(C)=CC=4)(=O)=O)[C:42]3=[N:43][CH:44]=2)=[CH:35][C:31]=1[C:32]([OH:34])=O)=[O:28].N1CCCC1.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>CN(C)C=O.C(O)(=O)C.CO>[CH3:25][O:26][C:27](=[O:28])[NH:29][C:30]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[C:41]3[C:47]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=4[O:54][CH3:55])=[CH:46][NH:45][C:42]3=[N:43][CH:44]=2)=[CH:35][C:31]=1[C:32]([N:13]1[CH2:14][CH2:15][CH2:16][CH2:11]1)=[O:34]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57731438HCID 57731438, compound

Product 1

HCID 57731467HCID 57731467, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (49.9 mg, 0.13 mmol) was added to a solution of 2-methoxycarbonylamino-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid (75 mg, 0.13 mmol), pyrrolidine (9.33, 0.13 mmol) and di-iso-propyl ethyl amine (51 mg, 0.39 mmol) in N,N-Dimethylformamide (1 ml). The reaction was stirred at room temperature for 1 hour, then methanol (2 ml) was added followed by aqueous sodium hydroxide (0.2 ml) and the reaction was stirred at room temperature for 16 hours. This solution was then neutralized with acetic acid and the compound was purified by preparative mass-triggered reverse-phase HPLC chromatography to give [4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(pyrrolidine-1-carbonyl)-phenyl]-carbamic acid methyl ester as a white solid.). 1H NMR (500 MHz, DMSO-d6) δ 1.81 (p, J=6 Hz 1H); 1.87 (p, J=6 Hz 1H); 3.41 (t, J=6 Hz 1H); 3.48 (t, J=6 Hz 1H); 3.65 (s, 3H); 3.81 (s, 3H); 7.04 (t, J=8 Hz 1H) 7.13 (d, J=8 Hz 1H); 7.29 (t, J=8 Hz, 1H); 7.60 (d, J=8 Hz 1H); 7.75 (m, 4H); 8.17 (s, 1H); 8.55 (s, 1H); 9.23 (s, br, 1H); 11.95 (s, br, 1H) (21.8 mg, 36% yield MS: m/z 471.5 (M+H+).

Workup

  1. stirringthe reaction was stirred at room temperature for 16 hours
  2. customthe compound was purified by preparative mass-triggered reverse-phase HPLC chromatography

Sources & evidence

ORD record
ord-e2802e9f5486400ab2f53459286a8507
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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