Trifluoroacetic acid → HCID 66785967, compound

HRID 1096677Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:31]C(=O)OC(C)(C)C)[CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([C:19]3[N:23]([CH2:24][CH2:25][F:26])[C:22]4[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=4[N:20]=3)[CH2:14]2)=[O:12])=[CH:4][CH:3]=1.[NH2:39][C:40]1[N:45]=[CH:44][C:43](B(O)O)=[CH:42][N:41]=1.C(O)(C(F)(F)F)=O.N[C@H](CC1C=CC(C2C=CC=CC=2)=CC=1)CC(N1CCC[C@@H](C2N(CCCOC)C3C=CC=CC=3N=2)C1)=O>>[NH2:31][C@H:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([C:43]2[CH:42]=[N:41][C:40]([NH2:39])=[N:45][CH:44]=2)=[CH:7][CH:6]=1)[CH2:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([C:19]2[N:23]([CH2:24][CH2:25][F:26])[C:22]3[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=3[N:20]=2)[CH2:14]1)=[O:12]

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 17750211(2-Aminopyrimidin-5-yl)boronic acid

HCID 56933214HCID 56933214, compound

HCID 66791847HCID 66791847, compound

Product 1

HCID 66785967HCID 66785967, compoundYield 14.4%

Procedure

Suzuki coupling of 145A with 2-aminopyrimidin-5-ylboronic acid (145E) was carried out analogously to the synthesis of Compound 613 (Example 6, Step B). The crude Boc-protected intermediate was de-protected with TFA using procedure similar to that for the synthesis of Compound 72 from Compound 6B (Example 6, Step C). The crude product was purified by preparative HPLC using 15% CH3CN/water as mobile phase. Compound 509 was obtained in 14.4% yield over two steps (17.8 mg), MS: MH+=502.4.

Workup

customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-b1ac20e3b9804136a61e4a957378c7f6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138168B1

Reaction notes

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