Diisopropylethylamine → HCID 86680552, compound

HRID 340107Notes

Reaction equation

HRID 340107 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-5864c73d72394f4198f72bc4907be19c
Source dataset
uspto-grants-2014_11
Patent number
US08895566B2

Reaction notes

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