1-Hydroxybenzotriazole → {(S)-3-Phenyl-2-[(2-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbonyl)-amino]-propyl}-carbamic acid tert-butyl ester

HRID 222112Notes

Reaction equation

HRID 222112 reaction equation
[C:1]1([C:7]2[NH:19][C:10]3=[C:11]4[C:16](=[CH:17][CH:18]=[C:9]3[C:8]=2[C:20](O)=[O:21])[CH:15]=[N:14][CH:13]=[CH:12]4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[C:32]([O:36][C:37](=[O:49])[NH:38][CH2:39][C@@H:40]([NH2:48])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:35])([CH3:34])[CH3:33].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:32]([O:36][C:37](=[O:49])[NH:38][CH2:39][C@@H:40]([NH:48][C:20]([C:8]1[C:9]2[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[N:14][CH:13]=[CH:12]3)[NH:19][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:21])[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53637716(S)-tert-Butyl (2-amino-3-phenylpropyl)carbamateHCID 687095872-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid

Product 1

HCID 68707419{(S)-3-Phenyl-2-[(2-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbonyl)-amino]-propyl}-carbamic acid tert-butyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid G2 (0.087 mmol) in DMF (1 mL), DIEA (0.26 mmol) and ((S)-2-amino-3-phenyl-propyl) -carbamic acid tert-butyl ester (0.13 mmol) were added. The mixture was cooled to 0° C., EDCI hydrochloride (0.13 mmol) and HOBT (0.13 mmol) were added and stirring was kept overnight at rt. The suspension was filtered and the solid was washed with aq saturated NaHCO3 and with water. After drying, the title compound was isolated in 43% yield. ESI (+) MS: m/z 521 (MH+). 1H NMR: 1.40 (s, 9H) 2.80-2.89 (m, 1H) 3.00-3.11 (m, 2H) 3.12-3.21 (m, 1H) 4.18-4.30 (m, 1H) 6.91-6.97 (m, 1H) 7.00-7.06 (m, 1H) 7.16-7.23 (m, 1H) 7.25-7.34 (m, 4H) 7.37-7.43 (m, 1H) 7.49-7.56 (m, 2H) 7.88 (d, J=7.62, 2H) 8.00 (d, J=9.00, 1H) 8.31 (d, J=9.00, 1H) 8.72 (s, 2H) 9.51 (s, 1H) 11.72 (bs, 1H).

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with aq saturated NaHCO3 and with water
  3. customAfter drying

Sources & evidence

ORD record
ord-ee6d9b0668c54683bc481363076f0244
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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