Sodium Carbonate → HCID 68782567, compound

HRID 79574Notes

Reaction equation

HRID 79574 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][CH:14]=[C:15]([NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[C:8]=23)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:22]([O:26][C:27]([N:29]([CH:42]([CH3:44])[CH3:43])[CH2:30][C@H:31]([C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[C:32](O)=[O:33])=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:17]([NH:16][C:15]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][C:7]=2[N:1]2[CH2:6][CH2:5][N:4]([C:32](=[O:33])[C@@H:31]([C:35]3[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=3)[CH2:30][N:29]([CH:42]([CH3:44])[CH3:43])[C:27](=[O:28])[O:26][C:22]([CH3:25])([CH3:23])[CH3:24])[CH2:3][CH2:2]2)[NH:13][CH:14]=1)(=[O:21])[CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 59564929(2S)-3-[tert-butoxycarbonyl(isopropyl)amino]-2-(4-chlorophenyl)propanoic acidHCID 68761562HCID 68761562, compound

Product 1

HCID 68782567HCID 68782567, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)butyramide (0.050 g, 0.174 mmol), (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (0.0625 g, 0.183 mmol, see Example H), HOBT-H2O (0.0373 g, 0.244 mmol), and EDCI (0.0434 g, 0.226 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.152 mL, 0.870 mmol) was then added, and the reaction was stirred at room temperature for 5 hours. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:10-500:20 DCM:MeOH) to give (S)-tert-butyl 3-(4-(3-butyramido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate (0.050 g, 47.0% yield).

Workup

  1. extractionextracted into DCM
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude residue that
  6. customwas purified by column chromatography (500:10-500:20 DCM:MeOH)

Sources & evidence

ORD record
ord-33d3a24b9f644aad8d89a3ffb1024784
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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