Formaldehyde → HCID 18354360, compound

HRID 429308Notes

Reaction equation

C(O[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:13][C@H:12]1[C@@H:30]([NH:32][C:33]1[N:38]=[C:37]([N:39]2[C:43]3[CH:44]=[CH:45][C:46]([C:48]4[CH:53]=[CH:52][N:51]=[C:50]([NH2:54])[N:49]=4)=[CH:47][C:42]=3[N:41]=[CH:40]2)[CH:36]=[CH:35][N:34]=1)[CH3:31])=O)C1C=CC=CC=1.C=O.[BH3-]C#N.[Na+]>>[CH3:9][N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:13][CH:12]1[CH:30]([NH:32][C:33]1[N:38]=[C:37]([N:39]2[C:43]3[CH:44]=[CH:45][C:46]([C:48]4[CH:53]=[CH:52][N:51]=[C:50]([NH2:54])[N:49]=4)=[CH:47][C:42]=3[N:41]=[CH:40]2)[CH:36]=[CH:35][N:34]=1)[CH3:31]

Participants

Reactant 3

HCID 712Formaldehyde

HCID 5003444Sodium cyanoborohydride

HCID 70212218HCID 70212218, compound

Product 1

HCID 18354360HCID 18354360, compound

Procedure

The title compound was prepared from (S,S)-2-[1-(1-(benzyloxycarbonyl)-4-(N-naphth-1-yl-carbamoyl)-piperazine-2-yl)-ethylamino]-4-[5-(2-amino-pyrimidin-4-yl)benzimidazol-1-yl]pyrimidine (5.5 mg), 37% aqueous formaldehyde (0.7 μL), and NaBH3CN (1 mg) according to the procedure described in EXAMPLE 14, Step G. 1H NMR (500 MHz, CDCl3): δ8.64 (s, 1H); 8.47 (d, J=1.5 Hz, 1H); 8.34-8.41 (m, 2H); 8.20 (d, J=8.5 Hz, 1H); 8.09 (dd, J=1.6, 8.5 Hz, 1H); 7.76-7.83 (m, 2H); 7.61 (t, J=7.1 Hz, 2H); 7.37-7.55 (m, 3H); 7.12 (d, J=5.5 Hz, 1H); 6.78 (d, J=5,5 Hz, 1H); 5.77 (br s, 1H); 5.13 (s, 2H); 4.50-4.60 (m, 1H); 4.09 (br d, J=12 Hz, 1H); 3.88 (br d, J=12 Hz, 1H); 3.20 (br t, J=11 Hz, 1H); 3.09 (dd, J=10, 13 Hz, 1H); 2.92 (br d, J=12 Hz, 1H) 2.40-2.60 (m, 5H); 1.36 (d, J=6.5 Hz, 3H). Mass spectrum (ESI) 431.2 (M-(N-naphthyl carbamoyl)+1).

Sources & evidence

ORD record: ord-f7451319c386478e9749aff947f7264d
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06316444B1

Reaction notes

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