Sodium Carbonate → HCID 68763597, compound

HRID 79557Notes

Reaction equation

HRID 79557 reaction equation
[CH3:1][C:2]1[C:10]2C(=NC=C(C3C=CC=CC=3)C=2N2CCNCC2)N[CH:3]=1.[NH2:23][C:24]([CH3:59])([CH3:58])[CH2:25][C@H:26]([C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=1)[C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[C:40]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43](F)[CH:42]=3)=[CH:39][N:38]=[C:37]3[NH:48][CH:49]=[CH:50][C:36]=23)[CH2:31][CH2:30]1)=[O:28].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.[CH3:82]CN(C(C)C)C(C)C.[C:91]([O-:94])([O-])=[O:92].[Na+].[Na+]>C(Cl)Cl>[Cl:57][C:54]1[CH:55]=[CH:56][C:51]([C@H:26]([C:27]([N:29]2[CH2:34][CH2:33][N:32]([C:35]3[C:40]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[CH:39][N:38]=[C:37]4[NH:48][CH:49]=[C:50]([CH3:82])[C:36]=34)[CH2:31][CH2:30]2)=[O:28])[CH2:25][C:24]([NH:23][C:91](=[O:92])[O:94][C:2]([CH3:10])([CH3:3])[CH3:1])([CH3:59])[CH3:58])=[CH:52][CH:53]=1

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 44198879HCID 44198879, compoundHCID 687614063-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68763597HCID 68763597, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.040 g, 0.110 mmol, see Example 15), (R)-4-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acid (0.0412 g, 0.120 mmol, Example 12), HOBT-H2O (0.0235 g, 0.153 mmol), and EDCI (0.0273 g, 0.142 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.0954 mL, 0.548 mmol) was then added, and the reaction was stirred at room temperature for 18 hours. The reaction was then poured into saturated Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, concentrated and purified (500:5 DCM:MeOH) to give (R)-tert-butyl 4-(4-chlorophenyl)-2-methyl-5-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-5-oxopentan-2-ylcarbamate (0.040 g, 59.3% yield).

Workup

  1. extractionextracted with DCM
  2. customThe combined organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified (500:5 DCM:MeOH)

Sources & evidence

ORD record
ord-4f8d12bed8cb4c8b8e1524737f40fea6
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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