HCID 18436703, compound → HCID 10165406, compound

HRID 456707Notes

Reaction equation

HRID 456707 reaction equation
BrC1C=C(Br)C2N(C(C(=O)C)=C(C3C=CC(F)=CC=3)N=2)C=1.[Br:22][C:23]1[CH:24]=[C:25]([Br:46])[C:26]2[N:27]([C:29]([C:39](=O)/[CH:40]=[CH:41]/N(C)C)=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[N:31]=2)[CH:28]=1.[CH:47]1([NH:52][C:53]([NH2:55])=[NH:54])[CH2:51][CH2:50][CH2:49][CH2:48]1>COC(OC)N(C)C>[CH:47]1([NH:52][C:53]2[N:55]=[C:39]([C:29]3[N:27]4[CH:28]=[C:23]([Br:22])[CH:24]=[C:25]([Br:46])[C:26]4=[N:31][C:30]=3[C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH:40]=[CH:41][N:54]=2)[CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

5

Reactant 3

HCID 18436703HCID 18436703, compoundHCID 18436707HCID 18436707, compoundHCID 178512468HCID 178512468, compound

Product 1

HCID 10165406HCID 10165406, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

In a similar manner as described in Example 1 treatment of 1-[6,8-dibromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]ethanone (850 mg, 2.1 mmol) with N,N-dimethylformamide dimethyl acetal (30 mL), followed by condensation of the resulting (2E)-1-[6,8-dibromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one with cyclopentyl guanidine gave N-cyclopentyl-4-[6,8-dibromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-2-pyrimidinamine (600 mg, 54% for two steps) as a yellow solid. 1H NMR (CDCl3): δ 9.98 (broad s, 1H), 8.13 (d, 1H), 7.71 (d, 1H), 7.68 (q, 2H), 7.14 (t, 2H), 6.40 (d, 1H), 5.61 (d, 1H), 4.36 (m, 1H), 2.0–2.2 (m, 2H), 1.4–2.0 (m, 6H); 19F NMR (CDCl3) δ −112.5; MS m/z 530 (M+1).

Sources & evidence

ORD record
ord-0bc66346986d44979e2f23f8f15ed065
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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