Trifluoroacetic acid → HCID 56645677, compound

HRID 2066416Notes

Reaction equation

HRID 2066416 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([O:12][CH:13]3[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[N:8]2[CH3:11])=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:3]=1.[CH2:30]([C:32]1[N:36](C2N=C3C(N=C(OC4CCNCC4)N3C)=C(N3CCOCC3)N=2)[C:35]2[CH:60]=[CH:61][CH:62]=[CH:63][C:34]=2[N:33]=1)[CH3:31].FC(F)(F)C(O)=O>>[NH:15]1[CH2:16][CH:13]([O:12][C:7]2[N:8]([CH3:11])[C:9]3[C:5]([N:6]=2)=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:3]=[C:2]([N:33]2[C:34]4[CH:63]=[CH:62][CH:61]=[CH:60][C:35]=4[N:36]=[C:32]2[CH2:30][CH3:31])[N:10]=3)[CH2:14]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 56645458HCID 56645458, compoundHCID 58054354HCID 58054354, compound

Product 1

HCID 56645677HCID 56645677, compound

Procedure

The compound was prepared from tert-butyl 3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidine-1-carboxylate in a similar manner as that of 4-(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-8-(piperidin-4-yloxy)-9H-purin-6-yl)morpholine, following General Procedures of Buchwald coupling shown in Scheme 3 and Boc-deprotection. The compound was used either as a mixture with unknown equivalent of trifluoroacetic acid or as a free base after treatment with aqueous base. Free base: 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=8.9 Hz, 1H), 7.74 (d, J=8.1 Hz, 1H), 5.66-5.54 (m, 1H), 4.22 (s, 4H), 4.08-3.99 (m, 2H), 3.94-3.79 (m, 6H), 3.63 (s, 3H), 3.40-3.25 (m, 3H), 1.43 (t, J=7.5 Hz, 3H). LCMS: M+H+=435.2.

Sources & evidence

ORD record
ord-7646335b4af247709f4f110fa5dde0b8
Source dataset
uspto-grants-2012_10
Patent number
US08293736B2

Reaction notes

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