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

HRID 914109Notes

Reaction equation

HRID 914109 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 the final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13-1.28 (m, 1H) 1.33-1.46 (m, 2H) 1.59-1.66 (m, 2H) 1.75-1.87 (m, 4H) 3.32 (s, 3H) 3.67-3.80 (m, 4H) 3.95 (s, 3H) 4.07 (t, 2H) 4.4-4.5 (m, 1H) 4.65-4.83 (m, 1H) 7.50 (d, J=8.3 Hz, 1H) 7.54 (d, J=1.5 Hz, 1H) 7.93 (s, 1H) 8.21 (s, 1H) 8.29 (d, J=8.1 Hz, 1H) 8.81 (d, J=6.8 Hz, 1H). [M+H] calc'd 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. customthe final compound was purified by reverse phase HPLC
  7. customto give the free base

Sources & evidence

ORD record
ord-0fc64544d1604b0c93c0daec8cb26273
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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