1-Pyrrolidinamine → HCID 25254618, compound

HRID 1880892Notes

Reaction equation

HRID 1880892 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](O)=[O:28])=[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(ON1[N:50]=[N:49][C:44]2[CH:45]=[CH:46][CH:47]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1(N)CCCC1>>[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]([NH:50][N:49]5[CH2:44][CH2:45][CH2:46][CH2:47]5)=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:8]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 279461-PyrrolidinamineHCID 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 25254618HCID 25254618, 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 pyrrolidin-1-amine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.45 (m, 3 H) 1.55-1.90 (m, 7 H) 2.02 (br. s., 4 H) 3.33 (s, 3 H) 3.52 (br. s., 4 H) 3.97 (s, 3 H) 4.14 (t, 2 H) 4.49 (quin, 1 H) 7.48 (d, 1 H) 7.52 (s, 1 H) 8.26 (s, 1 H) 8.31 (d, 1 H) 8.42 (s, 1 H). [M+H] calc'd for C26H33F2N7O3 530; found 530.

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-1707080a67f54a6bbcc594124c0f82d4
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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