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Hydrochloric Acid → N1-(4-(4-amino-1H-pyrrolo[3,2-c]pyridin-1-yl)phenyl)-N3-(4-fluorophenyl)malonarnide

HRID 230745
Notes
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Reaction equation

HRID 230745 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:37])[CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[C:28]4[CH:27]=[CH:26][N:25]=[C:24]([NH:29]C(=O)OC(C)(C)C)[C:23]=4[CH:22]=[CH:21]3)=[CH:16][CH:15]=2)=[O:12])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[NH2:29][C:24]1[C:23]2[CH:22]=[CH:21][N:20]([C:17]3[CH:16]=[CH:15][C:14]([NH:13][C:11](=[O:12])[CH2:10][C:9]([NH:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[O:37])=[CH:19][CH:18]=3)[C:28]=2[CH:27]=[CH:26][N:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57763151tert-Butyl 1-(4-(3-(4-fluorophenylamino)-3-oxopropanamido)phenyl)-1H-pyrrolo[3,2-c]pyridin-4-ylcarbamate

Product 1

HCID 11246660N1-(4-(4-amino-1H-pyrrolo[3,2-c]pyridin-1-yl)phenyl)-N3-(4-fluorophenyl)malonarnideYield 23.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 1-(4-(3-(4-fluorophenylamino)-3-oxopropanamido)phenyl)-1H-pyrrolo[3,2-c]pyridin-4-ylcarbamate (37 mg, 0.074 mmol) was treated with 4 N HCl in dioxane (2 mL) and stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between saturated NaHCO3 (2 mL) and EtOAc (2 mL). The EtOAc phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 10-15% MeOH-CHCl3 gradient elution) to afford the title compound (7.0 mg, 23%) as a white solid. 1H NMR (DMSO-d6) δ 10.58 (s, 1H), 10.38 (s, 1H), 8.01 (br s, 2H), 7.84 (d, 2H, J=9.0 Hz), 7.69-7.62 (m, 3H), 7.60 (d, 1H, J=7.4 Hz), 7.52 (d, 2H, J=9.0 Hz), 7.20-7.13 (m, 3H), 6.91 (d, 1H, J=8.2 Hz), 3.52 (s, 2H); LCMS (ESI+) m/z 404 (M+H)+; HPLC tR=2.98 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between saturated NaHCO3 (2 mL) and EtOAc (2 mL)
  3. customThe EtOAc phase was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2, 10-15% MeOH-CHCl3 gradient elution)

Sources & evidence

ORD record
ord-2ee3a038403140efabc5db2eef2bfbfe
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07566784B2

Reaction notes

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