Tert-butyl 3-aminoazetidine-1-carboxylate → HCID 25254000, compound

HRID 1880868Notes

Reaction equation

HRID 1880868 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=[N:49][C:44]2C=C[CH:47]=[N:48][C:43]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N1CC(N)C1)(OC(C)(C)C)=O>>[NH:48]1[CH2:43][CH:44]([NH:49][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][C:23]([NH:22][C:20]3[N:19]=[CH:18][C:9]4[N:10]([CH3:17])[C:11](=[O:16])[C:12]([F:14])([F:15])[CH2:13][N:7]([CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[C:8]=4[N:21]=3)=[C:24]([O:32][CH3:33])[CH:25]=2)[CH2:47]1

Participants

4

Reactant 3

HCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 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 25254000HCID 25254000, 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 3-amino azetidine. The final compound was purified by reverse phase HPLC and basified to give the free base. Further, after washing with water (10 ml), t-butoxycarbonyl (Boc) protection group was removed using 40% TFA in dichloromethane (6 ml) and purified the product using preparative HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22-1.85 (m, 10 H) 3.32 (s, 3 H) 3.35-3.41 (m, 1 H) 3.79 (br. s., 2 H) 3.95 (s, 3 H) 4.01-4.11 (m, 4 H) 4.47 (m, 1 H) 7.45-7.58 (m, 2 H) 7.93 (s, 1 H) 8.22 (s, 1 H) 8.30 (d, J=8.1 Hz, 1 H) 8.86 (br. d., 1 H). [M+H] calculated for C25H31F2N7O3, 516; found 516.

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
  4. washFurther, after washing with water (10 ml), t-butoxycarbonyl (Boc) protection group
  5. customwas removed
  6. custompurified the product

Sources & evidence

ORD record
ord-42b7cdc8b910413ba2515570bb9a4658
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

Loading…