1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 118890590, compound

HRID 919609Notes

Reaction equation

HRID 919609 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([N:8]([CH3:28])[C:9]2[C:10]3[CH:17]=[CH:16][N:15]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:50][C:51]1[CH:52]=[C:53]([NH:58][CH2:59][C:60](O)=[O:61])[CH:54]=[C:55]([Cl:57])[CH:56]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.CO.C(Cl)Cl>[Cl:50][C:51]1[CH:52]=[C:53]([NH:58][CH2:59][C:60]([N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([N:8]([CH3:28])[C:9]3[C:10]4[CH:17]=[CH:16][N:15]([S:18]([C:21]5[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=5)(=[O:19])=[O:20])[C:11]=4[N:12]=[CH:13][N:14]=3)[CH2:2]2)=[O:61])[CH:54]=[C:55]([Cl:57])[CH:56]=1

Participants

10

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 86706476HCID 86706476, compound

Product 1

HCID 118890590HCID 118890590, compoundYield 78.1%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(azepan-3-yl)-N-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (200 mg, 0.5 mmol), in DMF (4 mL) was added EDCI (144 mg, 0.75 mmol), HOBt (101 mg, 0.75 mmol), 2-(3,5-dichlorophenylamino)acetic acid (109 mg, 0.5 mmol) and DIEA (129 mg, 1.0 mmol) at 0° C. The reaction mixture was stirred at rt overnight and diluted with EtOAc (100 mL) and washed with water (50 mL). The aqueous layer was extracted with the EtOAc (50 mL), the combined organic layer was dried over Na2SO4 and evaporated in vacuo to give a residue that was subjected to flash column chromatography using 0-4% MeOH in CH2Cl2 as an eluent to give (235 mg, 77%) of the titled compound. LC-MS: m/z [M+1]=601.

Workup

  1. washwashed with water (50 mL)
  2. extractionThe aqueous layer was extracted with the EtOAc (50 mL)
  3. dry with materialthe combined organic layer was dried over Na2SO4
  4. customevaporated in vacuo
  5. customto give a residue that

Sources & evidence

ORD record
ord-48bf92d5eb1047b3a1cb634f8e054368
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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