Formaldehyde → 2-[1-(1-Methyl-4-(N-naphth-1-yi-carbamoyl)-piperazine-2-yl)-ethylamino]-4-[5-(3-ethyl-imidazolidin-2-on-1-yl)benzimidazol-1-yl]pyrimidine

HRID 429303Notes

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][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]([N:48]4[CH2:52][CH2:51][N:50]([CH2:53][CH3:54])[C:49]4=[O:55])=[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]([N:48]4[CH2:52][CH2:51][N:50]([CH2:53][CH3:54])[C:49]4=[O:55])=[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 183543732-[1-(1-(benzyloxycarbonyl)-4-(N-naphth-1-yl-carbamoyl)-piperazine-2-yl)-ethylamino]-4-[5-(3-ethyl-imidazolidin-2-on-1-yl)benzimidazol-1-yl]pyrimidine

Product 1

HCID 183543552-[1-(1-Methyl-4-(N-naphth-1-yi-carbamoyl)-piperazine-2-yl)-ethylamino]-4-[5-(3-ethyl-imidazolidin-2-on-1-yl)benzimidazol-1-yl]pyrimidine

Procedure

The title compound was prepared from 2-[1-(1-(benzyloxycarbonyl)-4-(N-naphth-1-yl-carbamoyl)-piperazine-2-yl)-ethylamino]-4-[5-(3-ethyl-imidazolidin-2-on-1-yl)benzimidazol-1-yl]pyrimidine (28 mg), 37% aqueous formaldehyde (19 μL), and NaBH3CN (4.8 mg) according to the procedure described in EXAMPLE 14, Step G. Mass spectrum (ESI) 619.3 (M+1).

Sources & evidence

ORD record: ord-37412047e89444ccabb1b0e676a80128
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06316444B1

Reaction notes

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