1-Pyrrolidineethanamine → HCID 57955650, compound

HRID 914110Notes

Reaction equation

HRID 914110 reaction equation
[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:58]1([CH2:63][CH2:64][NH2:65])[CH2:62][CH2:61][CH2:60][CH2:59]1>>[CH:1]1([N:7]2[CH2:13][C:12]([F:14])([F:15])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([NH:65][CH2:64][CH2:63][N:58]5[CH2:62][CH2:61][CH2:60][CH2:59]5)=[O:29])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252536804-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid

Product 1

HCID 57955650HCID 57955650, compound

Procedure

The title compound was synthesized from 4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and 2-(pyrrolidin-1-yl)ethanamine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (m, 1H) 1.38 (m, 2H) 1.65 (t, J=13.1 Hz, 3H) 1.79-1.92 (m, 6H) 2.03 (m, 2H) 3.08 (m, 2H) 3.33 (s, 3H) 3.35 (d, J=5.8 Hz, 2H) 3.61 (m, 4H) 3.96 (s, 3H) 4.12 (t, J=13.0 Hz, 2H) 4.40-4.58 (m, 1H) 7.53 (d, J=8.6 Hz, 1H) 7.56 (s, 1H) 8.22 (s, 1H) 8.24 (d, J=1.3 Hz, 1H) 8.29 (d, J=7.8 Hz, 1H) 8.7 (dd, J=10.1, 1.3 Hz, 1H). [M+H] calc'd for C28H37F2N7O3 558. found 558.

Workup

  1. customas described in the General procedure for amide bond synthesis
  2. customThe final compound was purified by reverse phase HPLC
  3. customto give the free base

Sources & evidence

ORD record
ord-6622d4de45714368b52a6aef80ae677c
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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