4-(4-chlorophenyl)morpholine → HCID 89775937, compound

HRID 2272997Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[N:7]=[CH:8][C:9]([C:11]3[C:12]4[N:13]([N:17]=[C:18]([NH2:20])[N:19]=4)[CH:14]=[CH:15][N:16]=3)=[CH:10][C:2]=12.Cl[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1.CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C>C(O)(C)(C)C>[O:31]1[CH2:32][CH2:33][N:28]([C:25]2[CH:26]=[CH:27][C:22]([NH:20][C:18]3[N:19]=[C:12]4[C:11]([C:9]5[CH:8]=[N:7][C:3]6=[N:4][CH:5]=[CH:6][N:1]=[C:2]6[CH:10]=5)=[N:16][CH:15]=[CH:14][N:13]4[N:17]=3)=[CH:23][CH:24]=2)[CH2:29][CH2:30]1

Participants

Conditions

Temperature: 65 °C

Procedure

8-Pyrido[2,3-b]pyrazin-7-yl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine, 4-(4-chloro-phenyl)-morpholine (1.1 eq.), chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-i-propyl-1,1′-biphenyl]2-(2-aminoethyl)phenyl)Pd(II) (0.25 eq), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-i-propyl-1,1′-biphenyl; BrettPhos (0.25 eq.) are combined and suspended in t-butanol. The suspension is purged with N2 and lithium bis(trimethylsilyl)amide, (3 eq; 20% (ca 1.06M) solution in THF/ethylbenzene) is added. The vessel is sealed under N2 and heated to 65° C. for 2 h and then to 110° C. for 2 h. The mixture is filtered and concentrated. Purification via prep. HPLC gives the title compound.

Workup

customThe suspension is purged with N2 and lithium bis(trimethylsilyl)amide, (3 eq; 20% (ca 1.06M) solution in THF/ethylbenzene)
additionis added
customThe vessel is sealed under N2
filtrationThe mixture is filtered
concentrationconcentrated
customPurification via prep

Sources & evidence

ORD record: ord-fe820b05ce644ab2a043d9377956b448
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120804B2

Reaction notes

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