Sodium Carbonate → HCID 86729646, compound

HRID 2284913Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[C:21]([O:25][C:26](=[O:43])[NH:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[C:36]([CH3:38])[C:35]([NH2:39])=[CH:34][C:33]=1[C:40](=[O:42])[NH2:41])([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C>C(O)CCCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:21]([O:25][C:26](=[O:43])[NH:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[C:36]([CH3:38])[C:35]([NH:39][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[C:5]([Cl:20])=[CH:4][N:3]=2)=[CH:34][C:33]=1[C:40](=[O:42])[NH2:41])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of N-(2-((2,5-dichloropyrimidin-4-yl)amino)phenyl)acrylamide (15 mg, 49 umol), tert-butyl(3-(4-amino-2-carbamoyl-5-methylphenoxy)propyl)carbamate (22 mg, 68 umol), and sodium carbonate (25 mg, 23 umol) in 1 mL of amyl alcohol under Ar, was added Pd2(dba)3 (9.6 mg) and DavePhos (15 mg). The resulting mixture was heated at 100° C. for 2 hr. After filtration, the product was purified by prep-HPLC, giving 18 mg of white powder (62%). MS: m/z 596.2 (ES+, M+H).

Workup

filtrationAfter filtration
customthe product was purified by prep-HPLC,

Sources & evidence

ORD record: ord-3e6be042df934cd79717c71b48976dae
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145387B2

Reaction notes

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