Diisopropylethylamine → HCID 86680552, compound

HRID 521346Notes

Reaction equation

HRID 521346 reaction equation
[N:1]([CH2:4][C@@H:5]([NH2:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=[N+:2]=[N-:3].[CH3:16][C@H:17]1[C:25]2[C:24]([C:26]3[S:30][C:29]([C:31](O)=[O:32])=[CH:28][CH:27]=3)=[N:23][CH:22]=[N:21][C:20]=2[CH2:19][CH2:18]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[N:1]([CH2:4][C@@H:5]([NH:15][C:31]([C:29]1[S:30][C:26]([C:24]2[C:25]3[C@H:17]([CH3:16])[CH2:18][CH2:19][C:20]=3[N:21]=[CH:22][N:23]=2)=[CH:27][CH:28]=1)=[O:32])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58465377HCID 58465377, compoundHCID 86658349HCID 86658349, compound

Product 1

HCID 86680552HCID 86680552, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-1-Azido-3-(2,4-dichlorophenyl)propan-2-amine (33 mg, 0.134 mmol) was added to a solution of (R)-5-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)thiophene-2-carboxylic acid (35 mg, 0.134 mmol) in DCM (0.7 mL). HBTU (56 mg, 0.148 mmol) was added, followed by DIPEA (0.23 mL, 1.34 mmol). The reaction mixture was stirred at room temperature for 1 hour. LC-MS of the reaction mixture showed no more starting material. The solvent was removed, and the resulting residue was purified on silica gel (0%-50% EtOAc/hexanes) gradient elution to yield N-((S)-1-azido-3-(2,4-dichlorophenyl)propan-2-yl)-5-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)thiophene-2-carboxamide as an oil (59 mg, 90%). m/z 486 (MH+).

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was purified on silica gel (0%-50% EtOAc/hexanes) gradient elution

Sources & evidence

ORD record
ord-c6a0b1bfb1da49e9baf5834a38d3dcec
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

Loading…