Diisopropylethylamine → HCID 60204494, compound

HRID 2267370Notes

Reaction equation

HRID 2267370 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:26]3[S:27][C:28]([Cl:31])=[CH:29][CH:30]=3)=[N:10][C:11]([NH:14][CH2:15][CH2:16][N:17]3[C:21]([CH3:23])([CH3:22])[C:20](=[O:24])[NH:19][C:18]3=[O:25])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[C:32]([N:39]([CH2:41][C:42](O)=[O:43])[CH3:40])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.CCOC(C)=O>[Cl:31][C:28]1[S:27][C:26]([C:9]2[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:42](=[O:43])[CH2:41][N:39]([CH3:40])[C:32](=[O:33])[O:34][C:35]([CH3:37])([CH3:38])[CH3:36])[CH:7]=[CH:6][CH:5]=3)=[CH:13][N:12]=[C:11]([NH:14][CH2:15][CH2:16][N:17]3[C:21]([CH3:22])([CH3:23])[C:20](=[O:24])[NH:19][C:18]3=[O:25])[N:10]=2)=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 60204493HCID 60204493, compound

Product 1

HCID 60204494HCID 60204494, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 50 mg (0.11 mmol) of 1-{2-[5-(3-aminophenyl)-4-(5-chlorothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethylimidazolidine-2,4-dione, 31 mg (0.16 mmol) of N-Boc-sarcosine, 31 mg (0.16 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 0.1 mg (0.01 mmol) of 4-dimethylaminopyridine and 0.057 mL (0.33 mmol) of N,N-diisopropylethylamine in 1 mL of CH2Cl2 was stirred for 18 h at rt. The reaction solution was poured into 75 mL of EtOAc and washed thrice with 2% (w/v) aqueous HCl, once with a saturated aqueous solution of NaHCO3, then with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography eluting with a linear gradient of neat EtOAc to 10% MeOH in EtOAc to yield the title compound. MS (M+H)+ 628.

Workup

  1. washwashed thrice with 2% (w/v) aqueous HCl
  2. dry with materialonce with a saturated aqueous solution of NaHCO3, then with brine, dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography
  6. washeluting with a linear gradient of neat EtOAc to 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-50cf14af2a5c4078b8d96ee435373dee
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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