4-Amino-1-Boc-piperidine → HCID 25254778, compound

HRID 914124Notes

Reaction equation

HRID 914124 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(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:65]1[CH2:70][CH2:69][CH:68]([NH2:71])[CH2:67][CH2:66]1)(OC(C)(C)C)=O>>[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:71][CH:68]5[CH2:69][CH2:70][NH:65][CH2:66][CH2:67]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 12682914-Amino-1-Boc-piperidineHCID 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 25254778HCID 25254778, 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 1-N—Boc 4-amino piperidine. Further, after washing with water (10 ml), t-butoxycarbonyl (Boc) protection group was removed using 40% TFA in dichloromethane (6 ml). The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.11-1.27 (m, 1H) 1.30-1.51 (m, 4H) 1.52-1.69 (m, 3H) 1.69-1.90 (m, 6H) 2.41-2.59 (m, 2H) 2.97 (d, J=12.38 Hz, 2H) 3.31 (s, 3H) 3.73-3.89 (m, 1H) 3.94 (s, 3H) 4.06 (t, J=13.52 Hz, 2H) 4.38-4.52 (m, 1H) 7.48 (dd, J=8.34, 1.77 Hz, 1H) 7.51 (d, J=1.77 Hz, 1H) 7.90 (s, 1H) 8.14 (d, J=7.83 Hz, 1H) 8.21 (s, 1H) 8.26 (d, J=8.34 Hz, 1H). [M+H] calc'd for C27H35F2N7O3 544. found 544.

Workup

  1. customas described in the General procedure for amide bond synthesis
  2. washFurther, after washing with water (10 ml), t-butoxycarbonyl (Boc) protection group
  3. customwas removed
  4. customThe final compound was purified by reverse phase HPLC
  5. customto give the free base

Sources & evidence

ORD record
ord-d93795049d8e4894b65ccf1d9516a204
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

Loading…