Ethylamine → HCID 131736372, compound

HRID 1055473Notes

Reaction equation

HRID 1055473 reaction equation
[CH2:1]([NH2:3])[CH3:2].[C:4]([O:8][C:9]([N:11]([CH3:51])[C@@H:12]([CH3:50])[C:13]([NH:15][C@H:16]1[C@H:22]([CH3:23])[O:21][C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[N:18]([CH2:28][C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]([C:38]3[CH:46]=[CH:45][C:41]([C:42]([OH:44])=O)=[CH:40][C:39]=3[C:47]#[N:48])[N:30]=2)[C:17]1=[O:49])=[O:14])=[O:10])([CH3:7])([CH3:6])[CH3:5].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>[NH4+].[Cl-]>[C:47]([C:39]1[CH:40]=[C:41]([C:42](=[O:44])[NH:3][CH2:1][CH3:2])[CH:45]=[CH:46][C:38]=1[N:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]([CH2:28][N:18]2[C:17](=[O:49])[C@@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([N:11]([CH3:51])[C:9](=[O:10])[O:8][C:4]([CH3:7])([CH3:5])[CH3:6])[CH3:50])[C@H:22]([CH3:23])[O:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]2=3)=[N:30]1)#[N:48]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 118574197HCID 118574197, compound

Product 1

HCID 131736372HCID 131736372, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

Ethylamine (100 μl, 200 μmol, Eq: 3.11) was added to a mixture of 4-(3-(((2S,3S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-methyl-4-oxo-3,4-dihydrobenzo[b][1,4]oxazepin-5(2H)-yl)methyl)-1H-indazol-1-yl)-3-cyanobenzoic acid (42 mg, 64.3 μmol, Eq: 1.00), DIEA (37.0 mg, 50 μl, 286 μmol, Eq: 4.45) and PyBOP (43.5 mg, 83.7 μmol, Eq: 1.3). After 16 h the mixture was diluted with sat. NH4Cl and extracted with EtOAc. The combined extracts were washed with sat. NaHCO3, NH4Cl, and H2O, then dried over Na2SO4 and concentrated to give a residue that was purified by preparative TLC to afford tert-butyl (S)-1-((2S,3S)-5-((1-(2-cyano-4-(ethylcarbamoyl)phenyl)-1H-indazol-3-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (40 mg, 92%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with sat. NaHCO3, NH4Cl, and H2O
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give a residue that
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-81db76c1da5d4af5854c2f23a6de8e31
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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