Ammonia → HCID 24989585, compound

HRID 222117Notes

Reaction equation

HRID 222117 reaction equation
[NH:1]1[C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[C:3]([C:14]([OH:16])=O)=[CH:2]1.C1C=CC2N(O)N=[N:23]C=2C=1.N.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:1]1[C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[C:3]([C:14]([NH2:23])=[O:16])=[CH:2]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 24989583HCID 24989583, compound

Product 1

HCID 24989585HCID 24989585, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,5-dihydro-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid E6 (0.093 mmol), HOBT.NH3 (0.374 mmol), TBTU (0.186 mmol) and DIEA (0.374 mmol) in DMF (5 mL) was stirred 4 h at rt. The solvent was evaporated and the crude residue was purified by preparative HPLC (Phase A: 0.05% NH4OH pH10/AN 95/5, Phase B: AN; gradient phase B 0—50% 8 min, yield 30%). ESI (+) MS: m/z 214 (MH+). 1H NMR: 2.83 (t, J=7.93, 2H), 2.98 (t, J=8.05, 2H), 6.61-7.28 (m, 2H), 7.33 (d, J=5.00, 1H), 7.56 (d, J=2.80, 1H), 8.28-8.38 (m, 2H), 11.85 (bs, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude residue was purified by preparative HPLC (Phase A
  3. customgradient phase B 0—50% 8 min, yield 30%

Sources & evidence

ORD record
ord-9f788c39b7044523b419488cd9e8e2f2
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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